Dimethylformamide → N-[4-(Benzylsulfanyl)-2-nitrophenyl]acetamide

HRID 1679441Notes

Reaction equation

HRID 1679441 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+].C(Br)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>O>[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([S:11][CH2:12][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:7][C:6]=1[N+:14]([O-:16])=[O:15])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 4311764Sodium borohydrideHCID 8180927Thiocyanic acid, 4-(acetylamino)-3-nitrophenyl ester

Product 1

HCID 20362823N-[4-(Benzylsulfanyl)-2-nitrophenyl]acetamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2.37 G. 1-acetamido-2-nitro-4-thiocyanatobenzene in 10 ml. dimethylformamide under nitrogen is treated with 0.38 g. sodium borohydride at 20°-25° C. After one hour 2.4 ml. benzylbromide is added, the mixture left for 2 hours, then diluted with water, filtered, washed with cyclohexane, recrystallized from methanol yielding 1-acetamido-2-nitro-4-benzylthiobenzene.

Workup

  1. customat 20°-25° C
  2. waitthe mixture left for 2 hours
  3. filtrationfiltered
  4. washwashed with cyclohexane
  5. customrecrystallized from methanol

Sources & evidence

ORD record
ord-85293db323a14b739ca39a336ec8f75e
Source dataset
uspto-grants-1978_03
Patent number
US04080461

Reaction notes

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