Dimethylformamide → 4-[(2-Ethoxyethyl)sulfanyl]-2-nitroaniline

HRID 1679467Notes

Reaction equation

HRID 1679467 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[CH2:22][CH2:23][O:24][CH2:25]C>O>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][CH2:25][O:24][CH2:23][CH3:22])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12]

Participants

6

Reactant 4

HCID 6228Dimethylformamide2×HCID 611412-Bromoethyl ethyl etherHCID 1046774-Amino-3-nitrophenyl thiocyanateHCID 4311764Sodium borohydride

Product 1

HCID 541915494-[(2-Ethoxyethyl)sulfanyl]-2-nitroaniline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

6 G. of 1-amino-2-nitro-4-thiocyanatobenzene in 20 ml. of dimethylformamide is treated under nitrogen with 1.17 g. of sodium borohydride in 10 ml. of dimethylformamide at not greater than 30° C. The mixture is stirred at 15° to 20° C for 1 hour, then treated with 5 g. of 2-bromoethyl ethylether at 20°-25° C. The mixture is heated to 100° C for 2 hours, then cooled and diluted with water. The product is extracted with chloroform and after drying of the chloroform solution with sodium sulfate, 1-amino-2-nitro-4-(2-ethoxyethylthio) benzene is obtained by evaporation of the solution.

Workup

  1. customat not greater than 30° C
  2. additiontreated with 5 g
  3. customat 20°-25° C
  4. temperaturecooled
  5. extractionThe product is extracted with chloroform
  6. dry with materialafter drying of the chloroform solution with sodium sulfate

Sources & evidence

ORD record
ord-b60df5aabdca49209a401283fca9cb49
Source dataset
uspto-grants-1978_03
Patent number
US04080461

Reaction notes

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