Sodium Hydroxide → 2-(4-Methoxy-3-propoxyphenyl)-4-(5-carbonyl-2-furyl)thiazole

HRID 1804871Notes

Reaction equation

HRID 1804871 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:10][CH:11]=[C:12]([C:14]3[O:15][C:16]([C:19](OC)=[O:20])=[CH:17][CH:18]=3)[N:13]=2)=[CH:5][C:4]=1[O:23][CH2:24][CH2:25][CH3:26].O1CCOCC1.[OH-].[Na+]>CO>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:10][CH:11]=[C:12]([CH:14]3[CH:18]=[CH:17][C:16](=[C:19]=[O:20])[O:15]3)[N:13]=2)=[CH:5][C:4]=1[O:23][CH2:24][CH2:25][CH3:26]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 185116982-(4-Methoxy-3-propoxyphenyl)-4-(5-methoxycarbonyl-2-furyl)thiazole

Product 1

HCID 865842582-(4-Methoxy-3-propoxyphenyl)-4-(5-carbonyl-2-furyl)thiazoleYield 47.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 970 mg of 2-(4-methoxy-3-propoxyphenyl)-4-(5-methoxycarbonyl-2-furyl)thiazole in 30 ml of methanol was added 20 ml of 1,4-dioxane and 5 ml of a 5 N aqueous sodium hydroxide solution. The reaction mixture was refluxed for 3 hours, then concentrated approximately 1/10. Water was added to the residue, and washed with ethyl acetate. To the aqueous layer was acidified with 5 N hydrochloric acid, and extracted with ethyl acetate. The combined organic layer was washed with water and a saturated aqueous sodium chloride solution, and dried with magnesium sulfate. Evaporation the solution, the residue was recrystallized from ethyl acetate to obtain 420 mg of 2-(4-methoxy-3-propoxyphenyl)-4-(5-carbonyl-2-furyl)thiazole as a white powder. mp. 191.0-192.0° C.

Workup

  1. temperatureThe reaction mixture was refluxed for 3 hours
  2. concentrationconcentrated approximately 1/10
  3. additionWater was added to the residue
  4. washwashed with ethyl acetate
  5. extractionextracted with ethyl acetate
  6. washThe combined organic layer was washed with water
  7. dry with materiala saturated aqueous sodium chloride solution, and dried with magnesium sulfate
  8. customEvaporation the solution
  9. customthe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-a1e7d7bc0a544513a9119fb36248199c
Source dataset
uspto-grants-2013_01
Patent number
US08354439B2

Reaction notes

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