Methyl 5-(2-bromoacetyl)furan-2-carboxylate → 2-(4-Methoxy-3-propoxyphenyl)-4-(5-methoxycarbonyl-2-furyl)thiazole

HRID 1804870Notes

Reaction equation

HRID 1804870 reaction equation
Br[CH2:2][C:3]([C:5]1[O:9][C:8]([C:10]([O:12][CH3:13])=[O:11])=[CH:7][CH:6]=1)=O.[CH3:14][O:15][C:16]1[CH:24]=[CH:23][C:19]([C:20]([NH2:22])=[S:21])=[CH:18][C:17]=1[O:25][CH2:26][CH2:27][CH3:28]>CO>[CH3:14][O:15][C:16]1[CH:24]=[CH:23][C:19]([C:20]2[S:21][CH:2]=[C:3]([C:5]3[O:9][C:8]([C:10]([O:12][CH3:13])=[O:11])=[CH:7][CH:6]=3)[N:22]=2)=[CH:18][C:17]=1[O:25][CH2:26][CH2:27][CH3:28]

Participants

4

Reactant 2

HCID 14945157Methyl 5-(2-bromoacetyl)furan-2-carboxylateHCID 185116974-Methoxy-3-propoxythiobenzamide

Product 1

HCID 185116982-(4-Methoxy-3-propoxyphenyl)-4-(5-methoxycarbonyl-2-furyl)thiazoleYield 79.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 877 mg of 5-(2-bromoacetyl)-2-methoxycarbonylfuran in 40 ml of methanol was added 800 mg of 4-methoxy-3-propoxythiobenzamide, and the mixture was refluxed for 1 hour. The reaction mixture was concentrated approximately ¼, then added diethyl ether. After cooling the solution, a precipitate was collected by filtration and dried to obtain 1.05 g of 2-(4-methoxy-3-propoxyphenyl)-4-(5-methoxycarbonyl-2-furyl)thiazole as a brown powder. mp. 141.0-142.0° C.

Workup

  1. temperaturethe mixture was refluxed for 1 hour
  2. concentrationThe reaction mixture was concentrated approximately ¼
  3. temperatureAfter cooling the solution
  4. filtrationa precipitate was collected by filtration
  5. customdried

Sources & evidence

ORD record
ord-a341428d4c7c4368b2946cb484b3c5cb
Source dataset
uspto-grants-2013_01
Patent number
US08354439B2

Reaction notes

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