Sodium hydride → HCID 12819358, compound

HRID 1105590Notes

Reaction equation

HRID 1105590 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][C:5]=1[NH:6][C:7]1[C:12]([N+:13]([O-:15])=[O:14])=[CH:11][C:10]([N+:16]([O-:18])=[O:17])=[CH:9][C:8]=1[C:19]([F:22])([F:21])[F:20].Cl[S:32][N:33]([CH3:44])[S:34]([C:37]1[CH:42]=[CH:41][C:40]([CH3:43])=[CH:39][CH:38]=1)(=[O:36])=[O:35]>C1COCC1>[Cl:3][C:4]1[CH:26]=[CH:25][C:24]([C:27]([F:28])([F:29])[F:30])=[CH:23][C:5]=1[N:6]([C:7]1[C:8]([C:19]([F:22])([F:21])[F:20])=[CH:9][C:10]([N+:16]([O-:18])=[O:17])=[CH:11][C:12]=1[N+:13]([O-:15])=[O:14])[S:32][N:33]([CH3:44])[S:34]([C:37]1[CH:42]=[CH:41][C:40]([CH3:43])=[CH:39][CH:38]=1)(=[O:36])=[O:35]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 104356Amidosulfenyl chloride, methyl[(4-methylphenyl)sulfonyl]-HCID 12797626Fentrifanil

Product 1

HCID 12819358HCID 12819358, compoundYield 66.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 0.25 g sodium hydride in 20 ml anhydrous THF was added 3.2 g of 2-[2'-chloro-5'-(trifluoromethyl)anilino]-3,5-dinitrobenzotrifluoride, in portions, at 10° to 20° C. After stirring for 30 minutes, a solution of 2 g of N-chlorothio-N-methyl-p-toluenesulfonamide in 20 ml dry THF was added rapidly at a temperature below -20° C. The mixture was stirred in an ice bath for 30 minutes, then quenched by careful addition of ether and water. The organic phase was washed once with water, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated in vacuo. The resultant oil was crystallized from a mixture of hexane and chlorobutane to give 3.2 g of N-[N-[2-chloro-5-(trifluoromethyl)-phenyl]-N-[2,4-dinitro-6-(trifluoromethyl)phenyl]-aminothio]-N,4-dimethylbenzenesulfonamide, mp 142.5°-144° C.

Workup

  1. customat 10° to 20° C
  2. stirringThe mixture was stirred in an ice bath for 30 minutes
  3. customquenched by careful addition of ether and water
  4. washThe organic phase was washed once with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated in vacuo
  8. customThe resultant oil was crystallized from a mixture of hexane and chlorobutane

Sources & evidence

ORD record
ord-a79a662d7c694f30be76d72088dc9d22
Source dataset
uspto-grants-1982_01
Patent number
US04309425

Reaction notes

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