O-Ethyl carbamothioate → 2-Hydroxy-5,6-dihydro-4H-benzothiazol-7-one

HRID 1580089Notes

Reaction equation

HRID 1580089 reaction equation
Cl[CH:2]1[C:7](=O)[CH2:6][CH2:5][CH2:4][C:3]1=[O:9].[C:10](=[S:15])([O:12]CC)[NH2:11]>O>[O:9]=[C:3]1[C:2]2[S:15][C:10](=[O:12])[NH:11][C:7]=2[CH2:6][CH2:5][CH2:4]1

Participants

4

Reactant 2

HCID 3032339O-Ethyl carbamothioateHCID 134833282-Chloro-1,3-cyclohexanedione

Product 1

HCID 64245982-Hydroxy-5,6-dihydro-4H-benzothiazol-7-oneYield 36.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 29.3 g of 2-chloro-1,3-cyclohexanedione [Muehlstaedt et al, J. Prakt Chem., Vol. 20 (1963), p. 285] and 21 g of ethyl thiocarbamate was heated at 140°C for 15 minutes and was then poured into water. The precipitate formed was recovered by vacuum filtering and was crystallized from isopropyl alcohol to obtain 12.2 g of 7-oxo-2,3,4,5,6,7-hexahydrobenzothiazoline-2-one melting at 262°C.

Workup

  1. customThe precipitate formed
  2. customwas recovered by vacuum
  3. filtrationfiltering
  4. customwas crystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-9a294540aabe4ec2b63d58a707f0442b
Source dataset
uspto-grants-1976_01
Patent number
US03932433

Reaction notes

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