Patent US3891703A successfully refreshed from Google Patents.
US3891703A
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Sulfamide process
Assignee: Mead Johnson and Co LLC
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Filing: 1973-09-20
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Granted: 1975-06-24
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Expires: 1993-09-20
Abstract
Abstract A process for preparing primary or secondary sulfamides under mild conditions which avoid halogenation or acylation of sensitive organic substituents involving cleavage of a substituted N-tert.-butyl sulfamide with trifluoroacetic acid is provided.
Inventors
- 👤 John D Catt
- 👤 William L Matier
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 05:01
CPC Classifications
C; C07; C07D; C07D213/00; C07D213/02; C07D213/04; C07D213/60; C07D213/72; C07D213/76
Claims Analysis
Total Claims: 8
Claim 1
Independent Claim
108 words
THE PROCESS FOR PREPARING AN N-SUBSTITUTED SULFAMIDE BEARING AT LEAST ONE HYDROGEN ATOM AND FROM 1 TO 3 ORGANIC GROUPS ATTACHED TO THE SULFAMIDE NITROGEN ATOMS THEREOF, AND ORGANIC GROUPS BEING STABLE UNDER THE REACTION CONDITIONS TO TRIFLUOROACETIC ACID AND HAVING MOLECULAR WEIGHTS OF FROM 17 TO 300 WHICH COMPRISES CONTACTING A SULFAMIDE BEARING AT LEAST ONE TERT-BUTYL GROUP AND SAID ORGANIC GROUPS ON THE SULFAMIDE NITROGEN ATOMS THEREOF WITH AT LEAST A MOLECULARLY EQUIVALENT AMOUNT OF TRIFLUOROACETIC ACID RELATIVE TO SAID TERT-BUTYL GROUP AT A TEMPERATURE OF FROM - 15*C. TO 40*C. FOR A TIME PERIOD SUFFICIENT TO RESULT IN REPLACEMENT OF SAID TERT-BUTYL GROUP WITH HYDROGEN.
Claim 2
Dependent Claim
108 words
THE PROCESS FOR PREPARING AN N-SUBSTITUTED SULFAMIDE BEARING AT LEAST ONE HYDROGEN ATOM AND FROM 1 TO 3 ORGANIC GROUPS ATTACHED TO THE SULFAMIDE NITROGEN ATOMS THEREOF, AND ORGANIC GROUPS BEING STABLE UNDER THE REACTION CONDITIONS TO TRIFLUOROACETIC ACID AND HAVING MOLECULAR WEIGHTS OF FROM 17 TO 300 WHICH COMPRISES CONTACTING A SULFAMIDE BEARING AT LEAST ONE TERT-BUTYL GROUP AND SAID ORGANIC GROUPS ON THE SULFAMIDE NITROGEN ATOMS THEREOF WITH AT LEAST A MOLECULARLY EQUIVALENT AMOUNT OF TRIFLUOROACETIC ACID RELATIVE TO SAID TERT-BUTYL GROUP AT A TEMPERATURE OF FROM - 15*C. TO 40*C. FOR A TIME PERIOD SUFFICIENT TO RESULT IN REPLACEMENT OF SAID TERT-BUTYL GROUP WITH HYDROGEN.
Claim 3
Dependent Claim
92 words
The process of claim 1 wherein said organic groups are selected from the group consisting of cycloalkyl, primary alkyl, secondary alkyl, aryl, primary aralkyl, secondary aralkyl, heterocyclic, heterocyclic wherein one of said sulfamide nitrogens is part of the heterocyclic ring, heterocycloalkyl, substituted cycloalkyl, primary substituted alkyl, secondary substituted alkyl, substituted aryl, primary substituted aralkyl, secondary substituted aralkyl, and substituted heterocyclic groups each wherein the substituent of said substituted groups is selected from the group consisting of halogen, lower alkoxy, lower alkyl, sulfamyl, nitro, cyano, carboxy, carbalkoxy, hydroxy, amino, carboxamide, and lower acyl.
Claim 4
Dependent Claim
22 words
The process of claim 1 wherein sufficient trifluoroacetic acid is used to provide a fluid reaction mixture and serve as reaction medium.
Claim 5
Dependent Claim
23 words
The process of claim 1 wherein about 5 to 15 ml. of trifluoroacetic acid is employed for each gram of said sulfamide reactant.
Claim 6
Dependent Claim
19 words
The process of claim 1 when carried out at ambient temperature in the range of from about 20*to 30*C.
Claim 7
Dependent Claim
20 words
The process of claim 1 wherein at least one of said organic groups is an aromatic carbocyclic or heterocyclic group.
Claim 8
Dependent Claim
16 words
The process of claim 1 wherein N-(4-acetylphenyl)-N''-(tert.-butyl)sulfamide is employed as starting material and N-(4-acetylphenyl)sulfamide is produced.
References Cited (Backward Citations)
No citation records indexed.
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1978-06-23 | 1978-12-23 | 1979-06-24 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1982-06-23 | 1982-12-23 | 1983-06-24 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1986-06-23 | 1986-12-23 | 1987-06-24 | $7700.00 | Window Closed / Lapsed |