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

HRID 596577Notes

Reaction equation

HRID 596577 reaction equation
[N+:1]([C:4]1[CH:10]=[C:9]([S:11][C:12]#N)[CH:8]=[CH:7][C:5]=1[NH2:6])([O-:3])=[O:2].CN(C)C=O.[BH4-].[Na+].[Cl:21][CH2:22][CH2:23]CBr>O.CC(C)=O>[N+:1]([C:4]1[CH:10]=[C:9]([S:11][CH2:12][CH2:23][CH2:22][Cl:21])[CH:8]=[CH:7][C:5]=1[NH2:6])([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 80061-Bromo-3-chloropropaneHCID 1046774-Amino-3-nitrophenyl thiocyanateHCID 4311764Sodium borohydride

Product 1

HCID 214502084-[(3-Chloropropyl)sulfanyl]-2-nitroaniline

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

6 G. of 2-nitro-4-thiocyanatoaniline in 30 ml. of dimethylformamide is treated under nitrogen with 1.2 g. of sodium borohydride at 20° to 30°. After 11/2 hours 15 ml. of acetone is added, followed 2 hours later by 10 g. of 3-chloropropylbromide. The mixture is left at 20°-25° for 16 hours, then diluted with water. The oily product is extracted into chloroform and passed through a silica column. 2-Nitro-4-(3-chloropropylthio)aniline is isolated by evaporation of the solvent.

Workup

  1. customat 20° to 30°
  2. custom2 hours 15 ml
  3. waitThe mixture is left at 20°-25° for 16 hours
  4. extractionThe oily product is extracted into chloroform

Sources & evidence

ORD record
ord-36cafb022df643e389cb0f7be98325bf
Source dataset
uspto-grants-1977_03
Patent number
US04011320

Reaction notes

Loading…