Dimethylformamide → 2-Nitro-4-[(2,2,2-trifluoroethyl)sulfanyl]aniline

HRID 1679469Notes

Reaction equation

HRID 1679469 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+].[F:21][C:22]([F:26])([F:25])CBr>O>[N+:11]([C:3]1[CH:4]=[C:5]([S:8][CH2:9][C:22]([F:26])([F:25])[F:21])[CH:6]=[CH:7][C:2]=1[NH2:1])([O-:13])=[O:12]

Participants

6

Reactant 4

HCID 6228Dimethylformamide2×HCID 678982-Bromo-1,1,1-trifluoroethaneHCID 1046774-Amino-3-nitrophenyl thiocyanateHCID 4311764Sodium borohydride

Product 1

HCID 540740062-Nitro-4-[(2,2,2-trifluoroethyl)sulfanyl]aniline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

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° to 20° C for 1 hour, then treated with 5 g. of 1,1,1-trifluoro-2-bromoethane at 20° to 25° C. The mixture is heated to 100° C for 3 hours, cooled and diluted with water. The mixture is extracted with chloroform and the chloroform solution is dried over sodium sulfate. 2-Nitro-4-(2,2,2-trifluoroethylthio) aniline is obtained upon evaporation of the solution.

Workup

  1. customat not greater than 30° C
  2. additiontreated with 5 g
  3. customat 20° to 25° C
  4. temperaturecooled
  5. extractionThe mixture is extracted with chloroform
  6. dry with materialthe chloroform solution is dried over sodium sulfate

Sources & evidence

ORD record
ord-bedb2452f7a047728eb6c76cb8f832d9
Source dataset
uspto-grants-1978_03
Patent number
US04080461

Reaction notes

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