Carbon Dioxide → HCID 16109207, compound

HRID 394284Notes

Reaction equation

HRID 394284 reaction equation
[C:1]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([NH2:11])=[S:10])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].Cl[CH:15]([C:21]([CH3:23])=O)[C:16]([O:18][CH2:19][CH3:20])=[O:17].C(=O)(O)[O-].[K+].C(=O)=O>C(O)C.O>[CH2:19]([O:18][C:16]([C:15]1[S:10][C:9]([C:8]2[CH:7]=[CH:6][C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])=[CH:13][CH:12]=2)=[N:11][C:21]=1[CH3:23])=[O:17])[CH3:20]

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 11858Ethyl 2-chloroacetoacetateHCID 516893Potassium BicarbonateHCID 27348174-tert-Butylbenzene-1-carbothioamide

Product 1

HCID 16109207HCID 16109207, compoundYield 87.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

The solution of 3.87 g (20 mmol) of 4-tert-butyl-thiobenzamide and 3.45 g (21 mmol) of ethyl 2-chloro-acetoacetate in 15 ml of ethanol was heated at reflux for 3 hours. Afterwards, the reaction mixture was cooled to ambient temperature and a solution of 3 g of potassium bicarbonate in 15 ml of water was added and the mixture was stirred until the gas evolution (CO2) had ceased. The compound was then extracted with 3 portions of 50 ml of tert-butyl methyl ether, the combined organic phases were washed with water, then with brine, dried over anhydrous sodium sulfate and finally evaporated. 5.3 g of 2-(4-tert-butyl-phenyl)-4-methyl-thiazole-5-carboxylic acid ethyl ester (87.4% of theory) were obtained as pale yellow viscous oil.

Workup

  1. temperatureat reflux for 3 hours
  2. extractionThe compound was then extracted with 3 portions of 50 ml of tert-butyl methyl ether
  3. washthe combined organic phases were washed with water
  4. dry with materialwith brine, dried over anhydrous sodium sulfate
  5. customfinally evaporated

Sources & evidence

ORD record
ord-f9027bc1fc504832a5e8d5015d370b4a
Source dataset
uspto-grants-2004_10
Patent number
US06809110B2

Reaction notes

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