Cesium carbonate → N-(4-Chloro-3-(cyclopentenyloxy)phenyl)thiazol-2-amine

HRID 1474003Notes

Reaction equation

HRID 1474003 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+].ClC[C:23]1[CH2:27][CH2:26][CH2:25][CH:24]=1>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][C:23]1[CH2:27][CH2:26][CH2:25][CH:24]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 129143891-(Chloromethyl)cyclopent-1-eneHCID 860960062-Chloro-5-(thiazol-2-ylamino)phenol

Product 1

HCID 86645047N-(4-Chloro-3-(cyclopentenyloxy)phenyl)thiazol-2-amineYield 25%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
60 °C

Procedure

Following the general procedure for O-allylation, Method B, a mixture 2-chloro-5-(thiazol-2-ylamino)phenol (88 mg, 0.39 mmol) and Cs2CO3 (127 mg, 0.39 mmol) in acetone was treated with 1-(chloromethyl)cyclopentene (60 mg, 0.39 mmol) at 0° C. The reaction mixture was heated to 60° C. and stirred for 3 h. The title compound was obtained after purification by flash chromatography on silica gel (hexane:EtOAc 8/2) in 25% yield (29 mg).

Sources & evidence

ORD record
ord-3da9da1998844294a504bc311b1f751f
Source dataset
uspto-grants-2015_04
Patent number
US09018209B2

Reaction notes

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