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

HRID 1414787Notes

Reaction equation

HRID 1414787 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][CH2:10][O:11][CH2:12][CH3:13])=[CH:4][C:3]=1[N+:14]([O-])=O.CO.S(S([O-])=O)([O-])=O.[Na+].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>O>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][CH2:10][O:11][CH2:12][CH3:13])=[CH:4][C:3]=1[NH2:14]

Participants

6

Reactant 4

HCID 887MethanolHCID 10340Sodium CarbonateHCID 24489Sodium DithioniteHCID 541915494-[(2-Ethoxyethyl)sulfanyl]-2-nitroaniline

Product 1

HCID 540506674-[(2-Ethoxyethyl)sulfanyl]benzene-1,2-diamine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

6.4 G. of 1-amino-2-nitro-4-(2-ethoxyethylthio) benzene in 100 ml. of methanol and 50 ml. of water is treated with 16 ml. of sodium dithionite and 14 g. sodium carbonate at reflux under nitrogen. Heating is continued for one-half hour, then the methanol is evaporated from the mixture. The mixtue is diluted with 100 ml. of water and is extracted with chloroform. The chloroform solution is dried over sodium sulfate and 1,2-diamino-4-(2-ethoxyethylthio) benzene is obtained by evaporation of the solution.

Workup

  1. temperatureHeating
  2. waitis continued for one-half hour
  3. customthe methanol is evaporated from the mixture
  4. additionThe mixtue is diluted with 100 ml
  5. extractionof water and is extracted with chloroform
  6. dry with materialThe chloroform solution is dried over sodium sulfate

Sources & evidence

ORD record
ord-78ebb3206a3e4df284e5c7294fc16d37
Source dataset
uspto-grants-1977_01
Patent number
US04002640

Reaction notes

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