Diethyl Ether → N-[4-chloro-3-(3-furylmethoxy)phenyl]thiazol-2-amine

HRID 1473994Notes

Reaction equation

HRID 1473994 reaction equation
[Cl: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:15]([O-])([O-])=O.[Cs+].[Cs+].[O:21]1[CH:25]=[CH:24][CH:23]=[C:22]1CBr.CCOCC>CC(C)=O>[Cl: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[O:14][CH2:15][C:23]1[CH:24]=[CH:25][O:21][CH:22]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 10796Cesium carbonateHCID 46037652-(Bromomethyl)furanHCID 860960062-Chloro-5-(thiazol-2-ylamino)phenol

Product 1

HCID 15956100N-[4-chloro-3-(3-furylmethoxy)phenyl]thiazol-2-amineYield 62%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Following the general procedure for O-alkylation, Method B, a mixture 2-chloro-5-(thiazol-2-ylamino)phenol (100 mg, 0.44 mmol) and Cs2CO3 (147 mg, 0.44 mmol) in acetone (4.4 mL) was treated with a freshly prepeared solution of 2-furylbromomethane in ether (125 mg, 0.48 mmol) at 0°. After 30 min the reaction was heated to RT. Reaction control by TLC showed full conversion after 5 h. The title compound was obtained after purification by flash chromatography on silica gel (hexane:EtOAc 3/1) in 62% yield (83 mg).

Workup

  1. customReaction control by TLC
  2. customafter 5 h

Sources & evidence

ORD record
ord-f2b8ae2cef024d1ea8c0615aaeb9facc
Source dataset
uspto-grants-2015_04
Patent number
US09018209B2

Reaction notes

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