Hydrochloric Acid → 8-Chloro-1,4-dihydro-2H-3,1-benzothiazine-2-thione

HRID 1414373Notes

Reaction equation

HRID 1414373 reaction equation
[NH2:1][C:2]1[C:9]([Cl:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4]O.[C:11](=[S:13])=[S:12].[OH-].[K+].Cl>C(O)C>[Cl:10][C:9]1[C:2]2[NH:1][C:11](=[S:12])[S:13][CH2:4][C:3]=2[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6348Carbon DisulfideHCID 14797Potassium HydroxideHCID 14155407(2-Amino-3-chlorophenyl)methanol

Product 1

HCID 214865688-Chloro-1,4-dihydro-2H-3,1-benzothiazine-2-thione

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 9 g. portion of 2-amino-3-chlorobenzyl alcohol was combined with 15 ml. of carbon disulfide and 5 g. of potassium hydroxide in 100 ml. of ethanol. The reaction mixture was stirred at reflux temperature overnight, and was then dumped into ice. After the aqueous mixture was acidified with hydrochloric acid, the product was extracted from the mixture with methylene chloride and was purified by chromatography over alumina with chloroform-hexane as the eluent. After recrystallization from methanol, 3,2 g. of 8-chloro-1,4-dihydro-2H-3,1-benzothiazin-2-thione, m.p. 125°-126° C., was obtained.

Workup

  1. temperatureat reflux temperature overnight
  2. extractionthe product was extracted from the mixture with methylene chloride
  3. customwas purified by chromatography over alumina with chloroform-hexane as the eluent
  4. customAfter recrystallization from methanol, 3,2 g

Sources & evidence

ORD record
ord-62c35d34fc5c46a49e35e0b44bc8bdf6
Source dataset
uspto-grants-1977_01
Patent number
US04001227

Reaction notes

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