Methanol → HCID 53868151, compound

HRID 1762337Notes

Reaction equation

HRID 1762337 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([CH3:14])[CH:11]=[CH:10][C:9]=2[S:15]([C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][C:18]=2[C:24]2[CH:29]=[CH:28][C:27]([NH2:30])=[C:26]([N+:31]([O-])=O)[CH:25]=2)=[O:16])=[CH:4][C:3]=1[N+:34]([O-])=O.CO.[S-2].[Na+].[Na+]>O>[NH2:34][C:3]1[CH:4]=[C:5]([C:8]2[CH:13]=[C:12]([CH3:14])[CH:11]=[CH:10][C:9]=2[S:15]([C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][C:18]=2[C:24]2[CH:29]=[CH:28][C:27]([NH2:30])=[C:26]([NH2:31])[CH:25]=2)=[O:16])[CH:6]=[CH:7][C:2]=1[NH2:1]

Participants

5

Reactant 3

HCID 887MethanolHCID 14804Sodium SulfideHCID 53642139(4-Amino-3-nitrophenyl)-4-methylphenyl sulfoxide

Product 1

HCID 53868151HCID 53868151, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of 21.2 g. (0.076 moles) of (4-amino-3-nitrophenyl)-4-methylphenyl sulfoxide in 80 ml. of methanol a solution of 22 g. (0.17 moles) of sodium sulfide of 60% purity in 25 ml. of water is added in one hour, under boiling. The reaction mixture is refluxed for 3 hours, and the progress of the reaction is monitored by thin layer chromatography. Thereafter 1 g. of celite is added to the reaction mixture, which is then filtered while hot. The filtrate is diluted with 50 ml. of water, and is slowly cooled to room temperature. The precipitate is filtered off, and the substance remaining on the filter is washed base-free with water. The product is then dried at 50° to 60° C. to yield 17 g. of the title compound, melting at 131° to 132° C.

Workup

  1. additionTo a suspension of 21.2 g
  2. temperatureThe reaction mixture is refluxed for 3 hours
  3. additionof celite is added to the reaction mixture, which
  4. filtrationis then filtered while hot
  5. additionThe filtrate is diluted with 50 ml
  6. filtrationThe precipitate is filtered off
  7. washis washed base-free with water
  8. customThe product is then dried at 50° to 60° C.
  9. customto yield 17 g

Sources & evidence

ORD record
ord-27b3740d1213426795506c02eafc5373
Source dataset
uspto-grants-1989_05
Patent number
US04831194

Reaction notes

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