Hydrochloric Acid → HCID 54407608, compound

HRID 2372817Notes

Reaction equation

HRID 2372817 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][CH:12]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[OH-].[K+].[CH3:21][N:22]([CH3:26])[C:23](Cl)=[S:24].Cl>O.CC(C)=O>[CH3:21][N:22]([CH3:26])[C:23](=[S:24])[O:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([C:11]2[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][CH:12]=2)(=[O:10])=[O:9])=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 27871Dimethylthiocarbamoyl chlorideHCID 21200841HCID 21200841, compound

Product 1

HCID 54407608HCID 54407608, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

2.36 g (0.0097 mol) of 4-[(4-hydroxyphenyl)sulfonyl]benzonitrile are added to a solution of 570 mg of potassium hydroxide in 35 ml of water. The solution is kept at room temperature for 15 minutes. After cooling to 0° C., a solution of 1.38 g of N,N-dimethylthiocarbamoyl chloride in 35 ml of acetone is added dropwise. After 4 hours, the reaction mixture is hydrolyzed in a 1 N solution of hydrochloric acid. The solution is extracted with ethyl acetate. The organic phase is washed with water until the pH of the washings is neutral, dried over magnesium sulfate and concentrated to dryness. 3 g (yield: 100%) of the expected product are thus obtained.

Workup

  1. waitAfter 4 hours
  2. extractionThe solution is extracted with ethyl acetate
  3. washThe organic phase is washed with water until the pH of the washings
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-fa4020e43d81475c8b8c8803fa891839
Source dataset
uspto-grants-1992_03
Patent number
US05100913

Reaction notes

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