Diethyl Ether → 2-Thiazolamine, N-[4-chloro-3-(2-furanylmethoxy)phenyl]-

HRID 1473991Notes

Reaction equation

HRID 1473991 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([O-])([O-])=O.[Cs+].[Cs+].[O:21]1[CH:25]=[CH:24][CH:23]=[C:22]1[CH2:26]Br.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][CH2:26][C:22]1[O:21][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 4

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

Product 1

HCID 159560982-Thiazolamine, N-[4-chloro-3-(2-furanylmethoxy)phenyl]-Yield 32%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Following the general procedure for O-alkylation, Method B, a mixture of 2-chloro-5-(thiazol-2-ylamino)phenol (100 mg, 0.44 mmol) and Cs2CO3 (152, 0.44 mmol) in acetone (4.4 mL) was treated with a freshly prepeared solution of 2-furylbromomethane in ether (0.75 mL, 0.44 mmol) at room temperature. Reaction control by TLC showed full conversion after 2 hrs. The title compound was obtained after purification by flash chromatography on silica gel (hexane:EtOAc 3/1) in 32% yield (43 mg).

Workup

  1. customReaction control by TLC
  2. customafter 2 hrs

Sources & evidence

ORD record
ord-de1b3f879f704c5695a08ab21c87e3cb
Source dataset
uspto-grants-2015_04
Patent number
US09018209B2

Reaction notes

Loading…