Iodine → 4-(2-Amino-1,3-thiazol-4-yl)phenol

HRID 1107000Notes

Reaction equation

HRID 1107000 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH3:9])=[CH:4][CH:3]=1.[NH2:11][C:12]([NH2:14])=[S:13].II>>[NH2:14][C:12]1[S:13][CH:9]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([OH:1])=[CH:3][CH:4]=2)[N:11]=1

Participants

4

Reactant 3

HCID 807IodineHCID 74694'-HydroxyacetophenoneHCID 2723790Thiourea

Product 1

HCID 3469264-(2-Amino-1,3-thiazol-4-yl)phenol

Procedure

According to Group 4-scheme 2, 4'-hydroxyacetophenone (Aldrich Chemical Co., Milwaukee, Wis., USA) was reacted with thiourea and iodine according to the method of R. M. Dodson and L. C. King, J. Amer. Chem. Soc. 1945, 67, 2242 to give 4-(2-amino-4-thiazolyl)phenol (5). Reaction of the latter compound with 1,1-dimethylethyl 2-bromoacetate in the presence of potassium carbonate gave 1,1-dimethylethyl 2-{4-(2-amino-4-thiazolyl)phenoxy}acetate (6). Subsequent hydrolysis of the later compound gave the thiazolylphenoxyacetic acid derivative of formula 2 wherein R1C is amino.

Sources & evidence

ORD record
ord-c8264594dbce4ff1bc35fd7e72c80d81
Source dataset
uspto-grants-2000_05
Patent number
US06057451

Reaction notes

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