2-(Dimethylsulfamoyl)benzene-1-sulfonyl isocyanate → 2-[[(4-Fluoro-6-trifluoromethoxypyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzenesulfonic acid N,N-dimethylamide

HRID 232529Notes

Reaction equation

HRID 232529 reaction equation
[CH3:1][N:2]([CH3:18])[S:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[S:12]([N:15]=[C:16]=[O:17])(=[O:14])=[O:13])(=[O:5])=[O:4].[NH2:19][C:20]1[N:25]=[C:24]([F:26])[CH:23]=[C:22]([O:27][C:28]([F:31])([F:30])[F:29])[N:21]=1>C(Cl)Cl>[CH3:1][N:2]([CH3:18])[S:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[S:12]([NH:15][C:16]([NH:19][C:20]1[N:25]=[C:24]([F:26])[CH:23]=[C:22]([O:27][C:28]([F:30])([F:31])[F:29])[N:21]=1)=[O:17])(=[O:13])=[O:14])(=[O:4])=[O:5]

Participants

4

Reactant 2

HCID 133926792-(Dimethylsulfamoyl)benzene-1-sulfonyl isocyanateHCID 150227162-Amino-4-fluoro-6-trifluoromethoxypyrimidine

Product 1

HCID 231784442-[[(4-Fluoro-6-trifluoromethoxypyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzenesulfonic acid N,N-dimethylamideYield 22%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5.9 g (20 mmol) of 2-(dimethylamino)sulfonylbenzenesulfonyl isocyanate were added to a solution of 4.0 g (20 mmol) of 2-amino-4-fluoro-6-trifluoromethoxypyrimidine in 30 ml of methylene chloride at 25° C. Stirring was carried out for 16 hours at 25° C., and the product which separated out was filtered off under suction, washed with a little ether and dried at 50° C. under reduced pressure from a water pump. 2.1 g of the title compound (22% of theory) of melting point 167°-169° C. were obtained in this manner. Further product can be isolated from the mother liquor.

Workup

  1. customthe product which separated out
  2. filtrationwas filtered off under suction
  3. washwashed with a little ether
  4. dry with materialdried at 50° C. under reduced pressure from a water pump

Sources & evidence

ORD record
ord-911512e5eaee41d1843e677e474443d5
Source dataset
uspto-grants-1997_01
Patent number
US05591694

Reaction notes

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