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Triethylamine → Chlorosulfamic acid

HRID 1584113
Notes
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Reaction equation

HRID 1584113 reaction equation
[Cl:1][S:2]([N:5]=C=O)(=[O:4])=[O:3].[F:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:16]([NH2:26])=[N:17][NH:18][C:19]=2[C:20]2[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=2)=[CH:11][CH:10]=1.[S:27](Cl)(=[O:30])(=[O:29])[NH2:28].C(N(CC)CC)C.[OH-].[NH4+]>C1C=CC=CC=1.C(#N)C.O>[S:2]([Cl:1])(=[O:4])(=[O:3])[NH2:5].[F:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[C:16]([NH:26][S:27]([NH2:28])(=[O:30])=[O:29])=[N:17][NH:18][C:19]=2[C:20]2[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=2)=[CH:13][CH:14]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

10

Reactant 5

HCID 8471TriethylamineHCID 14923Ammonium HydroxideHCID 24499Chlorosulfamic acidHCID 70918Chlorosulfonyl isocyanateHCID 15428649HCID 15428649, compound

Product 2

HCID 24499Chlorosulfamic acid
HCID 15428653
HCID 15428653, compound

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

Sulfamyl chloride was synthesized from chlorosulfonyl isocyanate according to the procedure described by R. Graf in Chemische Berichte, p. 509 (1959), which is incorporated herein by reference. A solution of 4-(4-fluorophenyl)-5-(4-pyridinyl)-1H-pyrazol-3-amine prepared as set forth in Example 2 (200 mg, 0.77 mmol), sulfamyl chloride (100 mg, 0.8 mmol) and triethylamine (200 mg, 2 mmol) in benzene (5 ml) and acetonitrile (5 ml) was stirred at room temperature for 2 hours. The reaction was stripped in vacuo and residue was treated with water and basified to pH 7 with ammonium hydroxide. The resultant precipitate was purified by chromatography on silica gel using mixtures of ethyl acetate and methanol as eluents. The purified [4-(4-fluorophenyl)-5-(4-pyridinyl)-1H-pyrazol-3-yl]sulfamide thus obtained had m.p. 201-202° C.

Workup

  1. customThe resultant precipitate was purified by chromatography on silica gel using mixtures of ethyl acetate and methanol as eluents

Sources & evidence

ORD record
ord-cc48edc554b1492b929f3c07ea5c06c9
Source dataset
uspto-grants-1999_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05932576

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes