Triethylamine → Chlorosulfamic acid

HRID 1369393Notes

Reaction equation

HRID 1369393 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

Participants

10

Reactant 5

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

Product 2

HCID 24499Chlorosulfamic acidHCID 15428653HCID 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-3be70d879881487a99236c2658ed6fae
Source dataset
uspto-grants-2003_06
Patent number
US06579873B2

Reaction notes

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