Water → HCID 14535767, compound

HRID 1904290Notes

Reaction equation

HRID 1904290 reaction equation
[CH3:1][C:2]1([CH3:19])[C:10]2[C:5](=[C:6]([NH:11][C:12](=[O:18])[CH:13](Cl)[C:14]([CH3:16])=O)[CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3]1.[C:20]([NH2:23])(=[S:22])[CH3:21].C(=O)([O-])[O-].[K+].[K+].O>O1CCCC1>[CH3:1][C:2]1([CH3:19])[C:10]2[C:5](=[C:6]([NH:11][C:12]([C:13]3[S:22][C:20]([CH3:21])=[N:23][C:14]=3[CH3:16])=[O:18])[CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 2723949ThioacetamideHCID 14535762HCID 14535762, compound

Product 1

HCID 14535767HCID 14535767, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.14 g (4.08 mmol) of N-(1,1-dimethyl-4-indanyl)-2-chloroacetoacetamide and 0.30 g (4.08 mmol) of thioacetamide were dissolved in 10 ml of tetrahydrofuran and was refluxed for 3 hours. To the reaction mixture was added 0.56 g (4.08 mmol) of anhydrous potassium carbonate and reaction was effected for 4 hours under reflux. The resulting solution was added to water and extracted with ethyl acetate. The organic layer was concentrated and then purified by column chromatography (eluent; n-hexane:ethyl acetate=50:50 V/V) to obtain 0.52 g of N-(1,1-dimethyl-4-indanyl)-2,4-dimethylthiazole-5-carboxamide (yield 43%).

Workup

  1. temperaturewas refluxed for 3 hours
  2. additionTo the reaction mixture was added
  3. temperatureunder reflux
  4. extractionextracted with ethyl acetate
  5. concentrationThe organic layer was concentrated
  6. custompurified by column chromatography (eluent; n-hexane:ethyl acetate=50:50 V/V)

Sources & evidence

ORD record
ord-c21f4c44ec334c318ac4e7b0b3cd9a0e
Source dataset
uspto-grants-1989_06
Patent number
US04837242

Reaction notes

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