Hydrochloric Acid → 2-Chloro-5-(thiazol-2-ylamino)phenol

HRID 1473971Notes

Reaction equation

HRID 1473971 reaction equation
Br[C:2]1[S:3][CH:4]=[CH:5][N:6]=1.[NH2:7][C:8]1[CH:9]=[CH:10][C:11]([Cl:15])=[C:12]([OH:14])[CH:13]=1.Cl>CCO>[Cl:15][C:11]1[CH:10]=[CH:9][C:8]([NH:7][C:2]2[S:3][CH:4]=[CH:5][N:6]=2)=[CH:13][C:12]=1[OH:14]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 764302-BromothiazoleHCID 806765-Amino-2-chlorophenol

Product 1

HCID 860960062-Chloro-5-(thiazol-2-ylamino)phenolYield 69%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

Following the general procedure for the synthesis of 2-R-5-(thiazol-2-ylamino)phenol, 2-bromothiazole (0.25 mL, 2.78 mmol), 5-amino-2-chlorophenol (200 mg, 1.39 mmol) and 37% HCl solution (0.24 mL, 2.78 mmol) in 10% aqueous EtOH solution (5 mL) was stirred at 90° C. for 24 h. The title compound was obtained after purification by flash chromatography on silica gel (hexane:EtOAc 7/3) in 69% yield (217 mg).

Sources & evidence

ORD record
ord-8f3004d8a769495da18fb5865c56c5de
Source dataset
uspto-grants-2015_04
Patent number
US09018209B2

Reaction notes

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