Dimethylformamide → HCID 68145278, compound

HRID 1658584Notes

Reaction equation

HRID 1658584 reaction equation
[H-].[Na+].[CH3:3][C:4]1[CH:9]=[CH:8][C:7]([SH:10])=[CH:6][CH:5]=1.CN(C)C=O.[C:16]([NH:19][C:20]1[CH:25]=[C:24](Cl)[CH:23]=[CH:22][C:21]=1[N+:27]([O-:29])=[O:28])(=[O:18])[CH3:17]>O>[C:16]([NH:19][C:20]1[CH:25]=[C:24]([S:10][C:7]2[CH:8]=[CH:9][C:4]([CH3:3])=[CH:5][CH:6]=2)[CH:23]=[CH:22][C:21]=1[N+:27]([O-:29])=[O:28])(=[O:18])[CH3:17]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 78114-MethylbenzenethiolHCID 24758Sodium hydrideHCID 224170n-(5-chloro-2-nitrophenyl)acetamide

Product 1

HCID 68145278HCID 68145278, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.84 G. of 57% sodium hydride is added to 3.0 g. p-methylthiophenol in 20 ml. dimethylformamide, 4.3 G. 2-acetamido-4-chloro-1-nitrobenzene is added and the mixture heated at 140°-145°C for 5 hours, cooled and treated with water. The crude product is filtered off, washed with water and pentane. Recrystallization from methanol gives 2-acetamido-4-(p-methylthiophenoxy)-1-nitrobenzene.

Workup

  1. temperaturethe mixture heated at 140°-145°C for 5 hours
  2. temperaturecooled
  3. filtrationThe crude product is filtered off
  4. washwashed with water and pentane
  5. customRecrystallization from methanol

Sources & evidence

ORD record
ord-bdd2278fb9d34143a360ad33e7329c78
Source dataset
uspto-grants-1976_06
Patent number
US03965113

Reaction notes

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