Potassium Carbonate → HCID 86645035, compound

HRID 1473983Notes

Reaction equation

HRID 1473983 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[S:10][CH:11]=[C:12]([CH3:14])[N:13]=2)=[CH:4][C:3]=1[OH:15].C([O-])([O-])=O.[K+].[K+].Br[CH2:23][CH:24]=[C:25]([CH3:27])[CH3:26]>CC(C)=O>[CH3:14][C:12]1[N:13]=[C:9]([NH:8][C:5]2[CH:6]=[CH:7][C:2]([CH3:1])=[C:3]([O:15][CH2:23][CH:24]=[C:25]([CH3:27])[CH3:26])[CH:4]=2)[S:10][CH:11]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 700922-Butene, 1-bromo-3-methyl-HCID 534390562-Methyl-5-[(4-methyl-1,3-thiazol-2-yl)amino]phenol

Product 1

HCID 86645035HCID 86645035, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Following the procedure general for O-alkylation, Method A, a mixture of 2-methyl-5-(4-methylthiazol-2-ylamino)phenol (79 mg, 0.36 mmol) and K2CO3 (54 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 56% yield (57 mg).

Workup

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

Sources & evidence

ORD record
ord-80a36f339c2a4ad2ad2a73d8fafd39e4
Source dataset
uspto-grants-2015_04
Patent number
US09018209B2

Reaction notes

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