1,3-Cyclohexanedione, 2-bromo-5,5-dimethyl- → 2-Amino-5,5-dimethyl-5,6-dihydro-4H-benzothiazol-7-one

HRID 1702185Notes

Reaction equation

HRID 1702185 reaction equation
Br[CH:2]1[C:7](=[O:8])[CH2:6][C:5]([CH3:10])([CH3:9])[CH2:4][C:3]1=O.[NH2:12][C:13]([NH2:15])=[S:14]>C(O)C.O.C(=O)(O)[O-].[Na+]>[NH2:15][C:13]1[S:14][C:2]2[C:7](=[O:8])[CH2:6][C:5]([CH3:10])([CH3:9])[CH2:4][C:3]=2[N:12]=1

Participants

6

Reactant 2

HCID 709581,3-Cyclohexanedione, 2-bromo-5,5-dimethyl-HCID 2723790Thiourea

Product 1

HCID 5878742-Amino-5,5-dimethyl-5,6-dihydro-4H-benzothiazol-7-oneYield 83.7%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 516892Sodium BicarbonateSolvent

Procedure

28 g of 2-bromo-5,5-dimethylcyclohexane-1,3-dione and 11.7 g of thiourea are dissolved in 200 ml of ethanol. After the weakly exothermic reaction has subsided, the mixture is refluxed for a further 6 hours. The solution is diluted with 400 ml of water and neutralised with saturated sodium bicarbonate solution. The precipitated crystals are collected by filtration and dried in vacuo at 80° C., affording 21 g of 2-amino-5,5-dimethyl-7-oxo-4,5-dihydro-6H-benzthiazole with a melting point of 203°-205° C.

Workup

  1. customAfter the weakly exothermic reaction
  2. temperaturethe mixture is refluxed for a further 6 hours
  3. filtrationThe precipitated crystals are collected by filtration
  4. customdried in vacuo at 80° C.

Sources & evidence

ORD record
ord-1107443d59d84ce4ab9c5456efada9c3
Source dataset
uspto-grants-1983_04
Patent number
US04380640

Reaction notes

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