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

HRID 1473975

Reaction equation

HRID 1473975 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]([CH:15]([CH3:17])[CH3:16])=[C:12]([OH:14])[CH:13]=1.Cl>CCO>[CH: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])([CH3:17])[CH3:16]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 764302-BromothiazoleHCID 598484345-Amino-2-isopropylphenol

Product 1

HCID 866450332-Isopropyl-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 (0.40 mL, 4.48 mmol), 5-amino-2-isopropylphenol (339 mg, 2.24 mmol) and 37% HCl solution (0.37 mL, 4.48 mmol) in 10% aqueous EtOH solution (10 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 (360 mg).

Sources & evidence

ORD record
ord-bbd09c215fdc421ea804aaf4bfac26bf
Source dataset
uspto-grants-2015_04
Patent number
US09018209B2

Linked notes

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