Water → HCID 13368505, compound

HRID 1154507Notes

Reaction equation

HRID 1154507 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8](=O)[N:7](C)[C:6]=2[CH:12]=1.O.[OH-].[K+]>C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([SH:9])=[C:6]([NH:7][CH3:8])[CH:12]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 129578365-Chloro-3-methyl-1,3-benzothiazol-2(3H)-one

Product 1

HCID 13368505HCID 13368505, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-Chloro-3-methyl-2-benzothiazolinone (70.0 g) was added to a mixture of water (118 ml), ethanol (350 ml) and potassium hydroxide (78.6 g). The solution was refluxed with stirring for three hours. After the solvent was evaporated under reduced pressure, the residual oil was dissolved in water. After removal of insoluble yellow crystals by filtration, the filtrate was neutralized with 2N-acetic acid, then resulting oily substance was extracted with ethyl acetate. The extract was washed with water, dried (Na2SO4), and evaporated to give oily 4-chloro-2-methylaminothiophenol (59.7 g). To a solution of sodium hydroxide (14.0 g) in water (100 ml) was added 4-chloro-2-methylaminothiophenol (59.6 g) with stirring, and then was added dropwise a solution of chloroacetic acid (34.0 g) in water (50 ml) at 20-25° C., followed by heating almost to boiling for three hours.

Workup

  1. temperatureThe solution was refluxed
  2. customAfter the solvent was evaporated under reduced pressure
  3. dissolutionthe residual oil was dissolved in water
  4. customAfter removal of insoluble yellow crystals
  5. filtrationby filtration
  6. extractionresulting oily substance was extracted with ethyl acetate
  7. washThe extract was washed with water
  8. dry with materialdried (Na2SO4)
  9. customevaporated

Sources & evidence

ORD record
ord-7c83e83a707c46f78b8873d6c7c336dd
Source dataset
uspto-grants-1984_12
Patent number
US04490292

Reaction notes

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