Triethylamine → 3-(Benzo-1,2,3-thiadiazole-7-carbonyloxy)-5,5-dimethyl-cyclohex-2-enone

HRID 6360

Reaction equation

HRID 6360 reaction equation
[CH3:1][C:2]1([CH3:10])[CH2:7][C:6](=[O:8])[CH2:5][C:4](=[O:9])[CH2:3]1.C(N(CC)CC)C.[S:18]1[C:22]2[C:23]([C:27](Cl)=[O:28])=[CH:24][CH:25]=[CH:26][C:21]=2[N:20]=[N:19]1>C(OCC)(=O)C>[S:18]1[C:22]2[C:23]([C:27]([O:8][C:6]3[CH2:7][C:2]([CH3:10])([CH3:1])[CH2:3][C:4](=[O:9])[CH:5]=3)=[O:28])=[CH:24][CH:25]=[CH:26][C:21]=2[N:20]=[N:19]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31358DimedoneHCID 183776071,2,3-Benzothiadiazole-7-carbonyl chloride

Product 1

HCID 197934183-(Benzo-1,2,3-thiadiazole-7-carbonyloxy)-5,5-dimethyl-cyclohex-2-enoneYield 87.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

5.6 g (0.04 mol) of 5,5-dimethyl-1,3-cyclohexanedione are dissolved in a mixture of 4.4 g (0.044 mol) of triethylamine and 120 ml of ethyl acetate. 8.7 g (0.044 mol) of benzothiadiazole-7-carboxylic acid chloride are added dropwise at 15° to 20° C., and the mixture is subsequently stirred overnight at room temperature. The ethyl acetate solution is washed with H2O, dried and concentrated. Purification by column chromatography using ethyl acetate/hexane gives 10.5 g (87.5%) of the title compound, melting point 131°-133° C.

Workup

  1. washThe ethyl acetate solution is washed with H2O
  2. customdried
  3. concentrationconcentrated
  4. customPurification by column chromatography

Sources & evidence

ORD record
ord-8e967b2fdeb8454a83c24e9d3bcde951
Source dataset
uspto-grants-1993_09
Patent number
US05248683

Linked notes

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