Pyrazole → HCID 15672100, compound

HRID 1086756Notes

Reaction equation

HRID 1086756 reaction equation
[CH3:1][NH:2][S:3](Cl)(=[O:5])=[O:4].[NH2:7][C:8]1[C:9]([Cl:26])=[CH:10][C:11]([Cl:25])=[C:12]([C:14]2[C:18]([Cl:19])=[C:17]([O:20][CH:21]([F:23])[F:22])[N:16]([CH3:24])[N:15]=2)[CH:13]=1.C(N(CC)CC)C.N1C=CC=N1>O1CCCC1.C(OCC)(=O)C>[Cl:19][C:18]1[C:14]([C:12]2[CH:13]=[C:8]([NH:7][S:3]([NH:2][CH3:1])(=[O:5])=[O:4])[C:9]([Cl:26])=[CH:10][C:11]=2[Cl:25])=[N:15][N:16]([CH3:24])[C:17]=1[O:20][CH:21]([F:22])[F:23]

Participants

7

Reactant 4

HCID 1048PyrazoleHCID 8471TriethylamineHCID 11789235N-Methylsulfamoyl chlorideHCID 15672098HCID 15672098, compound

Product 1

HCID 15672100HCID 15672100, compoundYield 71.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-Methylaminosulfonyl chloride (0.22 g, 1.67 mmoles) was added dropwise to a solution of 3-(5-amino-2,4-dichlorophenyl)-4-chloro-5-difluoromethoxy-1-methyl-1H-pyrazole (0.44 g, 1.28 mmoles) and triethylamine (0.17 g, 1.67 mmoles) in 20 ml anhydrous tetrahydrofuran under cooling with ice to react with the pyrazole derivative. After the addition was finished, the reaction was continued further for 2 hours. Then ethyl acetate was added to the reaction product solution, and the mixture was washed with water. The separated organic layer was dehydrated, concentrated, and purified by recrystallization from a n-hexane-ether mixture, giving the title compound (0.40 g), m.p. 133.0° C., yield 71.7%.

Workup

  1. temperatureunder cooling with ice
  2. additionAfter the addition
  3. washthe mixture was washed with water
  4. concentrationconcentrated
  5. custompurified by recrystallization from a n-hexane-ether mixture

Sources & evidence

ORD record
ord-c75ac408c7fc43c19f1b995cea4d04df
Source dataset
uspto-grants-1991_07
Patent number
US05032165

Reaction notes

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