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

HRID 616086Notes

Reaction equation

HRID 616086 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, under nitrogen, with 0.38 g. sodium borohydride at 20°-30° C. After one hour at 20°-30° C., 1.6 ml. of chloromethyl methyl ether is added. The mixture is stirred for a further 3 hour period, then diluted with water. The crude product is filtered off and recrystallized from cyclohexane, yielding 1-acetamido-2-nitro-4-methoxymethylthiobenzene.

Workup

  1. customat 20°-30° C
  2. filtrationThe crude product is filtered off
  3. customrecrystallized from cyclohexane

Sources & evidence

ORD record
ord-d6fb4c435f3a4444b619341409095e12
Source dataset
uspto-grants-1978_02
Patent number
US04072696

Reaction notes

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