Hydrochloric Acid → 2-(Phenylamino)benzenethiol

HRID 403139Notes

Reaction equation

HRID 403139 reaction equation
C[S-].[Na+].C[S:5][C:6]1[CH:18]=[CH:17][CH:16]=[CH:15][C:7]=1[NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.Cl>CN(C)P(N(C)C)(N(C)C)=O>[C:9]1([NH:8][C:7]2[CH:15]=[CH:16][CH:17]=[CH:18][C:6]=2[SH:5])[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4378561Sodium methanethiolateHCID 140448122-(methylthio)-N-phenylaniline

Product 1

HCID 6084822-(Phenylamino)benzenethiol

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Conditions

Temperature
140 °C

Procedure

A 250 mL round bottom flask was charged with sodium methanethiolate (5.18 g, 73.8 mmol), 2-(methylthio)-N-phenylaniline (13.25 g, 61.5 mmol) and hexamethyiphosphoramide (HMPA) (100 mL). The reaction mixture was heated up to 140° C. for 7 hours. The reaction was cooled to room temperature and 100 mL of 1N HCl was added. The reaction mixture was extracted with 3×100 mL ethyl acetate, the organic portion was washed with 3×50 mL brine, dried over sodium sulfate and evaporated to yield the desired compound. (12 g, 97%)

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. extractionThe reaction mixture was extracted with 3×100 mL ethyl acetate
  3. washthe organic portion was washed with 3×50 mL brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-3681f575aa494711a5498e8ba84afd96
Source dataset
uspto-grants-2014_06
Patent number
US08748011B2

Reaction notes

Loading…