Potassium Carbonate → HCID 86645038, compound

HRID 1473986Notes

Reaction equation

HRID 1473986 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[S:11][CH:12]=[C:13]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[N:14]=2)[CH:5]=[CH:6][C:7]=1[CH3:8].C([O-])([O-])=O.[K+].[K+].Br[CH2:27][CH:28]=[C:29]([CH3:31])[CH3:30]>CC(C)=O>[CH3:8][C:7]1[CH:6]=[CH:5][C:4]([NH:9][C:10]2[S:11][CH:12]=[C:13]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[N:14]=2)=[CH:3][C:2]=1[O:1][CH2:27][CH:28]=[C:29]([CH3:31])[CH3:30]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 700922-Butene, 1-bromo-3-methyl-HCID 72210847HCID 72210847, compound

Product 1

HCID 86645038HCID 86645038, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Following the general procedure for O-alkylation, Method A, a mixture of ethyl 2-(3-hydroxy-4-methylphenylamino)thiazole-4-carboxylate (80 mg, 0.29 mmol) and K2CO3 (44 mg, 0.32 mmol) in acetone (2.9 mL) was treated with 4-bromo-2-methyl-2-butene (0.037 mL, 0.32 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 57% yield (56 mg).

Workup

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

Sources & evidence

ORD record
ord-c88081081074454e9663f37de31ea2a1
Source dataset
uspto-grants-2015_04
Patent number
US09018209B2

Reaction notes

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