Dimethylformamide → 4-[(3-Bromopropyl)sulfanyl]-2-nitroaniline

HRID 1730821Notes

Reaction equation

HRID 1730821 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].CN(C)C=O.[BH4-].[Na+].[Br:21][CH2:22][CH2:23]CBr>O>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][CH2:23][CH2:22][Br:21])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 80011,3-DibromopropaneHCID 1046774-Amino-3-nitrophenyl thiocyanateHCID 4311764Sodium borohydride

Product 1

HCID 214965124-[(3-Bromopropyl)sulfanyl]-2-nitroaniline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5.85 G. of 1-amino-2-nitro-4-thiocyanatobenzene in 20 ml. dimethylformamide is treated under nitrogen with 1.14 g. sodium borohydride at not greater than 30°. The mixture is stirred for one hour at 15°-20°, then treated with 12 g. of 1,3-dibromopropane at 20°-25°. After a further 3 hours, water is added and the crude product extracted with chloroform. The dried chloroform solution is passed through a column of silica gel to remove polar material. Pure 1-amino-2-nitro-4-(3-bromopropylthio)benzene is obtained from the eluate.

Workup

  1. customat not greater than 30°
  2. additiontreated with 12 g
  3. customat 20°-25°
  4. waitAfter a further 3 hours
  5. extractionthe crude product extracted with chloroform
  6. customto remove polar material

Sources & evidence

ORD record
ord-217e2cd3061746c5ab31f86276279d9d
Source dataset
uspto-grants-1976_11
Patent number
US03993768

Reaction notes

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