Dimethylformamide → N-{4-[(Methoxymethyl)sulfanyl]-2-nitrophenyl}acetamide

HRID 1414775Notes

Reaction equation

HRID 1414775 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)[CH:19]=[O:20].[BH4-].[Na+].COCCl>O>[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([S:11][CH2:12][O:20][CH3:19])=[CH:7][C:6]=1[N+:14]([O-:16])=[O:15])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7864Chloromethyl Methyl EtherHCID 4311764Sodium borohydrideHCID 8180927Thiocyanic acid, 4-(acetylamino)-3-nitrophenyl ester

Product 1

HCID 20362834N-{4-[(Methoxymethyl)sulfanyl]-2-nitrophenyl}acetamide

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 1 hour 1.6 ml. of chloromethyl 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-methoxymethylthiobenzene.

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-86d2e3e52c4a46368ee081f6c78af3c7
Source dataset
uspto-grants-1977_01
Patent number
US04002640

Reaction notes

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