Potassium Carbonate → HCID 86645037, compound

HRID 1473985Notes

Reaction equation

HRID 1473985 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[S:10][CH:11]=[C:12]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[N:13]=2)[CH:5]=[CH:6][CH:7]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:26][CH:27]=[C:28]([CH3:30])[CH3:29]>CC(C)=O>[CH3:29][C:28]([CH3:30])=[CH:27][CH2:26][O:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[S:10][CH:11]=[C:12]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[N:13]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 700922-Butene, 1-bromo-3-methyl-HCID 72210846HCID 72210846, compound

Product 1

HCID 86645037HCID 86645037, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Following the general procedure for O-alkylation, Method A, a mixture of ethyl 2-(3-hydroxyphenylamino)thiazole-4-carboxylate (182 mg, 0.69 mmol) and K2CO3 (105 mg, 0.76 mmol) in acetone (6.9 mL) was treated with 4-bromo-2-methyl-2-butene (0.096 mL, 0.83 mmol). The reaction mixture was heated at reflux for 4 h. The title compound was obtained after purification by flash chromatography on silica gel (hexane:EtOAc 7/3) in 55% yield (127 mg).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 4 h

Sources & evidence

ORD record
ord-15d1eca583f74753902cbed51c350187
Source dataset
uspto-grants-2015_04
Patent number
US09018209B2

Reaction notes

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