Sodium hydride → HCID 19018480, compound

HRID 1109983Notes

Reaction equation

HRID 1109983 reaction equation
[H-].[Na+].[F:3][C:4]([F:17])([F:16])[C:5]1[CH:15]=[CH:14][CH:13]=[CH:12][C:6]=1[CH2:7][S:8]([NH2:11])(=[O:10])=[O:9].[H][H].[Cl:20][C:21]1[N:26]=[C:25]([C:27](Cl)=[O:28])[CH:24]=[C:23]([CH3:30])[N:22]=1>C(COC)OC>[F:17][C:4]([F:16])([F:3])[C:5]1[CH:15]=[CH:14][CH:13]=[CH:12][C:6]=1[CH2:7][S:8]([NH:11][C:27]([C:25]1[CH:24]=[C:23]([CH3:30])[N:22]=[C:21]([Cl:20])[N:26]=1)=[O:28])(=[O:9])=[O:10]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 107263662-CHLORO-6-METHYL-4-PYRIMIDINECARBONYL CHLORIDEHCID 142756951-[2-(Trifluoromethyl)phenyl]methanesulfonamideHCID 178418361HCID 178418361, compound

Product 1

HCID 19018480HCID 19018480, compoundYield 35.4%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

0.44 g of sodium hydride suspension (60% strength in mineral oil) is added to a stirred solution of 2.4 g of 2-trifluoromethylbenzylsulfonamide in 40 ml of dimethoxyethane and stirring is continued until the evolution of hydrogen is complete. A solution of 2-chloro-6-methylpyrimidine-4-carbonyl chloride (from 2.1 g of carboxylic acid, 20 ml of dioxane, [lacuna] drops of dimethylformamide and 2.1 g of thionyl chloride) in 20 ml of dimethoxyethane is rapidly added dropwise to this. The mixture is then stirred at room temperature for 3 h and worked up as described in Example 13. 1.4 g of 2-trifluoromethyl-N-[(2-chloro-6-methylpyrimidin-4-yl)carbonyl]benzylsulfonamide of melting point 198°-199° C. are obtained in this way.

Workup

  1. stirringThe mixture is then stirred at room temperature for 3 h

Sources & evidence

ORD record
ord-5519e89eddc44bcd87b082145f9b9f63
Source dataset
uspto-grants-1994_06
Patent number
US05324710

Reaction notes

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