Dimethylformamide → 1-Acetamido-2-nitro-4-methoxyethylthiobenzene

HRID 596585Notes

Reaction equation

HRID 596585 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([S:11][C:12]#N)=[CH:7][C:6]=1[N+:14]([O-:16])=[O:15])(=[O:3])[CH3:2].CN(C)C=O.[BH4-].[Na+].[CH3:24][O:25][CH2:26]CCl>O>[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([S:11][CH2:12][CH2:24][O:25][CH3:26])=[CH:7][C:6]=1[N+:14]([O-:16])=[O:15])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 123162-Chloroethyl methyl etherHCID 4311764Sodium borohydrideHCID 8180927Thiocyanic acid, 4-(acetylamino)-3-nitrophenyl ester

Product 1

HCID 540479021-Acetamido-2-nitro-4-methoxyethylthiobenzene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2.37 G. of 1-acetamido-2-nitro-4-thiocyanatobenzene in 10 ml. dimethylformamide is treated at 20°-25° C under nitrogen, with 0.38 g. of sodium borohydride. After one hour 1.6 ml. of chloroethyl methyl ether is added, and the mixture kept at 20°-30° C for a further three hours. Water is then added and the product filtered off. Recrystallization from cyclohexane gives 1-acetamido-2-nitro-4-methoxyethylthiobenzene.

Workup

  1. waitthe mixture kept at 20°-30° C for a further three hours
  2. filtrationthe product filtered off
  3. customRecrystallization from cyclohexane

Sources & evidence

ORD record
ord-21e64aaf5a1f47faa60620149eacef62
Source dataset
uspto-grants-1977_03
Patent number
US04011320

Reaction notes

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