1,3-Cyclohexanedione, 2-bromo-5,5-dimethyl- → HCID 3123575, compound

HRID 1702186Notes

Reaction equation

HRID 1702186 reaction equation
Br[CH:2]1[C:7](=[O:8])[CH2:6][C:5]([CH3:10])([CH3:9])[CH2:4][C:3]1=O.C([O-])(=O)C.[Na+].[CH3:17][NH:18][C:19]([NH2:21])=[S:20]>C(O)(=O)C>[CH3:17][NH:18][C:19]1[S:20][C:2]2[C:7](=[O:8])[CH2:6][C:5]([CH3:10])([CH3:9])[CH2:4][C:3]=2[N:21]=1

Participants

5

Reactant 3

HCID 709581,3-Cyclohexanedione, 2-bromo-5,5-dimethyl-HCID 517045Sodium AcetateHCID 2723704Methylthiourea

Product 1

HCID 3123575HCID 3123575, compoundYield 81.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

82 g of 2-bromo-5,5-dimethylcyclohexane-1,3-dione, 40 g of sodium acetate and 50 g of N-methylthiourea are dissolved in 500 ml of acetic acid. The mixture is stirred at room temperature until the weakly exothermic reaction has subsided, and then refluxed for 3 hours. The reaction mixture is then concentrated to one third of its volume in a rotary evaporator, poured into 100 ml of water and cooled to 0° C. The precipitate is collected by filtration and dried in vacuo at 80° C., affording 64 g of 2-methylamino-5,5-dimethyl-7-oxo-4,5-dihydro-6H-benzthiazole with a melting point of 217°-218° C.

Workup

  1. temperaturerefluxed for 3 hours
  2. concentrationThe reaction mixture is then concentrated to one third of its volume in a rotary evaporator
  3. additionpoured into 100 ml of water
  4. temperaturecooled to 0° C
  5. filtrationThe precipitate is collected by filtration
  6. customdried in vacuo at 80° C.

Sources & evidence

ORD record
ord-aa00dd27246240d9a70a7ba0ce1cd3d7
Source dataset
uspto-grants-1983_04
Patent number
US04380640

Reaction notes

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