Water → 2-Amino-4-nitrobenzenethiol

HRID 1896772Notes

Reaction equation

HRID 1896772 reaction equation
F[C:2]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:3]=1[NH2:4].O.O.O.O.O.O.O.O.O.[S-2:21].[Na+].[Na+].C(=O)(O)[O-].[Na+].O>ClCCl>[NH2:4][C:3]1[CH:5]=[C:6]([N+:9]([O-:11])=[O:10])[CH:7]=[CH:8][C:2]=1[SH:21]

Participants

6

Reactant 4

HCID 962WaterHCID 677852-Fluoro-5-nitroanilineHCID 73972Sodium sulfide nonahydrateHCID 516892Sodium Bicarbonate

Product 1

HCID 63364002-Amino-4-nitrobenzenethiolYield 100.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
125 °C

Procedure

2-Fluoro-5-nitroaniline (1 g, 6.41 mmol), sodium sulfide nonahydrate (1.7 g, 7.05 mmol), sodium bicarbonate (600 mg, 7.05 mmol) and water (15 mL) were combined and heated in the microwave at 125° C. for 5 min. After cooling, dichloromethane was added, and the organic layer was washed with 2M aqueous hydrochloric acid and then brine. The combined organic layers were dried over anhydrous MgSO4 and evaporated to afford 1.1 g (33%) of the title compound.

Workup

  1. temperatureAfter cooling
  2. washthe organic layer was washed with 2M aqueous hydrochloric acid
  3. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  4. customevaporated

Sources & evidence

ORD record
ord-e9c5997c6d844913b6436a312ef63ad8
Source dataset
uspto-grants-2013_08
Patent number
US08518980B2

Reaction notes

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