Diethyl Ether → N-(3-(Furan-2-ylmethoxy)-4-methylphenyl)thiazol-2-amine

HRID 1473990Notes

Reaction equation

HRID 1473990 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[S:10][CH:11]=[CH:12][N:13]=2)=[CH:4][C:3]=1[OH:14].C([O-])([O-])=O.[Cs+].[Cs+].[O:21]1[CH:25]=[CH:24][CH:23]=[C:22]1[CH2:26]Br.CCOCC>CC(C)=O>[O:21]1[CH:25]=[CH:24][CH:23]=[C:22]1[CH2:26][O:14][C:3]1[CH:4]=[C:5]([NH:8][C:9]2[S:10][CH:11]=[CH:12][N:13]=2)[CH:6]=[CH:7][C:2]=1[CH3:1]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 10796Cesium carbonate2×HCID 46037652-(Bromomethyl)furanHCID 866450292-Methyl-5-(thiazol-2-ylamino)phenol

Product 1

HCID 86645041N-(3-(Furan-2-ylmethoxy)-4-methylphenyl)thiazol-2-amineYield 36%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Following the general procedure for O-alkylation, Method B, a mixture of 2-methyl-5-(thiazol-2-ylamino)phenol (100 mg, 0.48 mmol) and Cs2CO3 (158 mg, 0.48 mmol) in acetone (4.4 mL) was treated with a freshly prepared solution of 2-furylbromomethane in ether (0.85 mL, 0.44 mmol) at room temperature. After 2 h Cs2CO3 (150 mg, 0.46 mmol) was added and stirred for 5.5 h at rt. The title compound was obtained after purification by flash chromatography on silica gel (hexane:EtOAc 3/1) in 36% yield (50 mg).

Sources & evidence

ORD record
ord-4eeb0d18dbda4684b88c93b578629d41
Source dataset
uspto-grants-2015_04
Patent number
US09018209B2

Reaction notes

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