Potassium Carbonate → HCID 86645034, compound

HRID 1473982Notes

Reaction equation

HRID 1473982 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([NH:7][C:8]2[CH:9]=[C:10]([OH:14])[CH:11]=[CH:12][CH:13]=2)[S:5][CH:6]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:22][CH:23]=[C:24]([CH3:26])[CH3:25]>CC(C)=O>[CH3:1][C:2]1[N:3]=[C:4]([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH2:22][CH:23]=[C:24]([CH3:26])[CH3:25])[CH:9]=2)[S:5][CH:6]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 700922-Butene, 1-bromo-3-methyl-HCID 534394803-[(4-Methyl-1,3-thiazol-2-yl)amino]phenol

Product 1

HCID 86645034HCID 86645034, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Following the procedure general for O-alkylation, Method A, a mixture of 3-(4-methylthiazol-2-ylamino)phenol (74 mg, 0.36 mmol) and K2CO3 (55 mg, 0.39 mmol) in acetone (3.6 mL) was treated with 4-bromo-2-methyl-2-butene (0.05 mL, 0.43 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 59% yield (58 mg).

Workup

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

Sources & evidence

ORD record
ord-dd9b30b2615548968c5f2ffa9e68c973
Source dataset
uspto-grants-2015_04
Patent number
US09018209B2

Reaction notes

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