Benzenesulfinic acid, sodium salt → 2-Amino-3-cyano-5-formyl-4-phenylsulfonylthiophene

HRID 1591301Notes

Reaction equation

HRID 1591301 reaction equation
[C:1]1([S:7]([O-:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Na+].[NH2:11][C:12]1[S:13][C:14]([CH:20]=[O:21])=[C:15](Cl)[C:16]=1[C:17]#[N:18]>O>[NH2:11][C:12]1[S:13][C:14]([CH:20]=[O:21])=[C:15]([S:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)(=[O:9])=[O:8])[C:16]=1[C:17]#[N:18]

Participants

4

Reactant 2

HCID 2723840Benzenesulfinic acid, sodium saltHCID 27376122-Amino-4-chloro-5-formyl-3-thiophenecarbonitrile

Product 1

HCID 138792242-Amino-3-cyano-5-formyl-4-phenylsulfonylthiopheneYield 83%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 82 parts of sodium phenylsulfinate in 500 parts of water is added to a mixture of 93.3 g of 2-amino-4-chloro-3-cyano-5-formylthiophene an 500 parts of methylglycol, and the reaction mixture is heated at the boil for 6 hours. Thereafter, the solution is filtered while hot and the filtrate is left to stand overnight. The precipitated product is then filtered off under suction, washed with water and dried. 121 parts (83% of theory) of 2-amino-3-cyano-5-formyl-4-phenylsulfonylthiophene are obtained.

Workup

  1. temperaturethe reaction mixture is heated at the boil for 6 hours
  2. filtrationThereafter, the solution is filtered while hot and the filtrate
  3. waitis left
  4. filtrationThe precipitated product is then filtered off under suction
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-c097305c49444c68816d24638c9acec1
Source dataset
uspto-grants-1993_04
Patent number
US05206375

Reaction notes

Loading…