Benzyl Bromide → N-(3-(benzyloxy)-4-chlorophenyl)thiazol-2-amine

HRID 1474000Notes

Reaction equation

HRID 1474000 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+].[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CC(C)=O>[CH2:21]([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[Cl:1])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 860960062-Chloro-5-(thiazol-2-ylamino)phenol

Product 1

HCID 15956108N-(3-(benzyloxy)-4-chlorophenyl)thiazol-2-amineYield 53%

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 (50 mg, 0.22 mmol) and Cs2CO3 (72 mg, 0.22 mmol) in acetone (4.4 mL) was treated with benzyl bromide (38 mg, 0.22 mmol) at RT. Reaction control by TLC showed full conversion after 2 h. The title compound was obtained after purification by flash chromatography on silica gel (hexane:EtOAc 7/3) in 53% yield (37 mg).

Workup

  1. customReaction control by TLC
  2. customafter 2 h

Sources & evidence

ORD record
ord-2a032a163ce24841b159f0853d3e4014
Source dataset
uspto-grants-2015_04
Patent number
US09018209B2

Reaction notes

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