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Derivatives of substituted urea, acyl ureas, and sulphonyl ureas, and a process for producing the same

Assignee: Sucreries Du Soissonnais et Scuriere Cie
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Filing: 1974-11-13
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Granted: 1977-03-22
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Expires: 1994-11-13
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Abstract

Abstract A process for the production of compounds of the general formula: ##STR1## and compounds of that general formula, in which A represents hydrogen or an R 1 -- X group (in which X represents --CO or --SO 2 and R 1 represents an optionally substituted alkyl, cycloalkyl, aralkyl, alkoxy, aryl, aryloxy, etheroxy, aliphatic or aromatic group), R 2 represents a hydrogen atom or an optionally substituted alkyl, cycloalkyl, aralkyl, or aryl group, and R 3 represents a hydrogen atom or an alkyl group derived from a secondary or tertiary alcohol, particularly a tertio-butyl group, with the restriction that, when R 2 represents hydrogen, R 3 represents the said alkyl group and that, when R 3 represents hydrogen, R 2 represents the said optionally substituted alkyl, cycloalkyl, aralkyl, or aryl group, the said process comprising reacting a cyanamide of the formula: ##STR2## (in which A and R 2 have the meanings given above) with a compound e.g. a tertiary or secondary alcohol adapted to form readily a carbo cation (R 3 + ) in the presence of a catalyst e.g. sulphuric acid or a Lewis acid.

Inventors

  • 👤 Jesus Anatol
  • 👤 Jean Berecoechea

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-09 04:25
CPC Classifications
C; C07; C07C; C07C311/00; C07C311/50; C07C311/52; C07C311/54; C07C311/55; C07C275/00; C07C275/46; C07C275/58; C07C275/60; C07C311/01; C07C311/12; C07C311/13; C07C311/57; C07C311/58

Claims Analysis

Total Claims: 6
Claim 1
Independent Claim 158 words
A process for producing compounds of the general formula: ##STR121## in which A is hydrogen or a monovalent group R 1 -- X (in which X is --CO or --SO 2 , and R 1 is alkyl, cycloalkyl, aralkyl, alkoxy, aryl, aryloxy, or etheroxy), R 2 is hydrogen, alkyl, cyclo-alkyl, aralkyl, or aryl, and R 3 is hydrogen or an alkyl radical derived from a secondary or tertiary alcohol, with the restriction that, when R 2 is hydrogen, R 3 is alkyl and that when R 3 is hydrogen, R 2 is alkyl, cycloalkyl, aralkyl, or aryl, said process comprising reacting a cyanamide of the formula: ##STR122## (in which A and R 2 have the meanings given above), with a compound adapted to readily form a carbo cation (R 3 + ) selected from the group consisting of tertiary alcohols, secondary alcohols and unsaturated compounds, in the presence of a catalyst of sulfuric acid or a Lewis acid.
Claim 2
Dependent Claim 158 words
A process for producing compounds of the general formula: ##STR121## in which A is hydrogen or a monovalent group R 1 -- X (in which X is --CO or --SO 2 , and R 1 is alkyl, cycloalkyl, aralkyl, alkoxy, aryl, aryloxy, or etheroxy), R 2 is hydrogen, alkyl, cyclo-alkyl, aralkyl, or aryl, and R 3 is hydrogen or an alkyl radical derived from a secondary or tertiary alcohol, with the restriction that, when R 2 is hydrogen, R 3 is alkyl and that when R 3 is hydrogen, R 2 is alkyl, cycloalkyl, aralkyl, or aryl, said process comprising reacting a cyanamide of the formula: ##STR122## (in which A and R 2 have the meanings given above), with a compound adapted to readily form a carbo cation (R 3 + ) selected from the group consisting of tertiary alcohols, secondary alcohols and unsaturated compounds, in the presence of a catalyst of sulfuric acid or a Lewis acid.
Claim 3
Dependent Claim 13 words
A process according to claim 1, in which the catalyst is sulphuric acid.
Claim 4
Dependent Claim 28 words
A process according to claim 1, in which the catalyst is boron fluoroetherate and the reaction is effected in the presence of a solvent for the starting cyanamide.
Claim 5
Dependent Claim 26 words
A process according to claim 1 wherein R 3 is tertiary butyl, and said compound adapted to readily form a carbo cation is tertiary butyl alcohol.
Claim 6
Dependent Claim 36 words
A process according to claim 1 wherein R 3 is an alkyl derived from a tertiary alcohol, and said compound adapted to readily form a carbo cation is selected from the group consisting of tertiary alcohols.

References Cited (Backward Citations)

US3427323A Cited
US3332994A Cited
US3748356A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1980-03-21 1980-09-20 1981-03-22 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1984-03-21 1984-09-20 1985-03-22 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1988-03-21 1988-09-20 1989-03-22 $7700.00 Window Closed / Lapsed

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