Dimethylformamide → [(4-Amino-3-nitrophenyl)sulfanyl]acetonitrile

HRID 1679476Notes

Reaction equation

HRID 1679476 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]#N)=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].[CH3:14][N:15](C)C=O.[BH4-].[Na+].ClCC#N>O>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][C:14]#[N:15])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12]

Participants

6

Reactant 4

HCID 6228Dimethylformamide2×HCID 7856ChloroacetonitrileHCID 1046774-Amino-3-nitrophenyl thiocyanateHCID 4311764Sodium borohydride

Product 1

HCID 20362816[(4-Amino-3-nitrophenyl)sulfanyl]acetonitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4.4 G. of 1-amino-2-nitro-4-thiocyanatobenzene in 10 ml. of dimethylformamide is treated under nitrogen with 0.85 g. of sodium borohydride in 10 ml. of DMF at not greater than 30° C. The mixture is stirred at 15° C. to 20° C. for one hour, then treated with 5 g. of chloroacetonitrile at 20° C. to 25° C. The mixture is treated overnight at room temperature and poured into water. Filtration and recrystallization from methanol affords 1-amino-2-nitro-4-cyanomethylthiobenzene.

Workup

  1. customat not greater than 30° C
  2. additiontreated with 5 g
  3. customat 20° C. to 25° C
  4. additionThe mixture is treated overnight at room temperature
  5. filtrationFiltration and recrystallization from methanol

Sources & evidence

ORD record
ord-51a655e738cf41cb895199ae104c0085
Source dataset
uspto-grants-1978_03
Patent number
US04080461

Reaction notes

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