Methanol → 4-[(2,2,2-Trifluoroethyl)sulfanyl]benzene-1,2-diamine

HRID 1679470Notes

Reaction equation

HRID 1679470 reaction equation
[N+:1]([C:4]1[CH:10]=[C:9]([S:11][CH2:12][C:13]([F:16])([F:15])[F:14])[CH:8]=[CH:7][C:5]=1[NH2:6])([O-])=O.CO>[Fe].O>[NH2:6][C:5]1[CH:7]=[CH:8][C:9]([S:11][CH2:12][C:13]([F:16])([F:14])[F:15])=[CH:10][C:4]=1[NH2:1]

Participants

5

Reactant 2

HCID 887MethanolHCID 540740062-Nitro-4-[(2,2,2-trifluoroethyl)sulfanyl]aniline

Product 1

HCID 544871614-[(2,2,2-Trifluoroethyl)sulfanyl]benzene-1,2-diamine

Reagents, catalysts & solvents 2

HCID 23925IronCatalyst2×HCID 962WaterSolvent

Procedure

4.1 G. of 2-nitro-4-(2,2,2-trifluoroethylthio) aniline in 60 ml. of methanol and 12 ml. of water is treated with 1.25 g. of ferrous sulfate and 3.3. g. of iron powder at reflux. After 2 hours, 1.25 g. of ferrous sulfate and 3.3 g. of iron powder are added and heating is continued for 4 hours. The mixture is poured into 600 ml. of hot tetrahydrofuran and filtered. 1,2-Diamino-4-(2,2,2-trifluoroethylthio) benzene is obtained from the filtrate by evaporation.

Workup

  1. temperatureheating
  2. waitis continued for 4 hours
  3. additionThe mixture is poured into 600 ml
  4. filtrationof hot tetrahydrofuran and filtered

Sources & evidence

ORD record
ord-8e9470e7d84b46489ca755b9bd82a1f1
Source dataset
uspto-grants-1978_03
Patent number
US04080461

Reaction notes

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