Acetic Acid → Benzothiazole, 6-chloro-2-methyl-

HRID 4703Notes

Reaction equation

HRID 4703 reaction equation
[Na].[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](N)=O)=[C:5]([SH:13])[CH:4]=1.[C:14](O)(=O)C>O>[Cl:2][C:3]1[CH:8]=[CH:7][C:6]2[N:9]=[C:10]([CH3:14])[S:13][C:5]=2[CH:4]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 5360545SodiumHCID 212741484-Chloro-2-mercaptophenylurea

Product 1

HCID 138133Benzothiazole, 6-chloro-2-methyl-Yield 93.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

112.25 parts of the sodium salt of 4-chloro-2-mercaptophenylurea, which salt is obtainable according to Example 6 of European Pat. No. 0,039,483, are suspended in 450 parts of glacial acetic acid in an autoclave. The pressure vessel is closed and heated slowly to 150° C.-160° C. in the course of 2 hours, a pressure of about 5 bar being established. The water formed is discharged continuously via a pressure release valve. The reaction is complete after 5 hours. The autoclave is cooled to room temperature and opened, the reaction mixture is allowed to run into 1000 parts of water, and the precipitated 6-chloro-2-methylbenzothiazole is isolated by filtration, washed neutral and dried in vacuo at 40° C. 85.6 parts of a product of the formula ##STR21## of melting point 85° C.-86° C. are obtained; this corresponds to a yield of 93.3% of theory, based on sodium salt employed.

Workup

  1. customThe pressure vessel is closed
  2. temperatureheated slowly to 150° C.-160° C. in the course of 2 hours
  3. customis discharged continuously via a pressure release valve

Sources & evidence

ORD record
ord-933065a153024599baa544ac59e11817
Source dataset
uspto-grants-1988_02
Patent number
US04727154

Reaction notes

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