1,3-Dichloroacetone → 4-(Chloromethyl)-2-(4-methoxyphenyl)-1,3-thiazole

HRID 394344

Reaction equation

HRID 394344 reaction equation
C(OC(=O)C(OCC)CC1C=CC(O)=CC=1C)C.[CH3:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[S:28][CH:29]=[C:30]([CH2:32]CO)[N:31]=2)=[CH:23][CH:22]=1.COC1C=CC(C(N)=S)=CC=1.[Cl:46]CC(CCl)=O>>[Cl:46][CH2:32][C:30]1[N:31]=[C:27]([C:24]2[CH:25]=[CH:26][C:21]([O:20][CH3:19])=[CH:22][CH:23]=2)[S:28][CH:29]=1

Participants

5

Reactant 4

HCID 107931,3-DichloroacetoneHCID 7368274-MethoxybenzenecarbothioamideHCID 226475992-[2-(4-Methoxy-phenyl)-thiazol-4-yl]-ethanolHCID 57792490[Rac]-2-ethoxy-3-(4-hydroxy-2-methyl-phenyl)-propionic acid ethyl ester

Product 1

HCID 25176564-(Chloromethyl)-2-(4-methoxyphenyl)-1,3-thiazole

Procedure

In analogy to the procedure described in example 10 c], [rac]-2-ethoxy-3-(4-hydroxy-2-methyl-phenyl)-propionic acid ethyl ester (example 10 b]) was reacted with 2-[2-(4-methoxy-phenyl)-thiazol-4-yl]-ethanol (prepared from 4-methoxy-thiobenzamide and 1,3-dichloroacetone in analogy to the procedure described in example 4 a] to yield 4-chloromethyl-2-(4-methoxy-phenyl)-thiazole, followed by side chain elongation in analogy to the sequence described in example 13 a] to 13 d]) in the presence of triphenylphosphine and di-tert-butyl azodicarboxylate to yield [rac]-2-ethoxy-3-(4-{2-[2-(4-methoxy-phenyl)-thiazol-4-yl]-ethoxy}-2-methyl-phenyl)-propionic acid ethyl ester as light yellow solid.

Sources & evidence

ORD record
ord-335550ae9fc843339d48866feed1bb3d
Source dataset
uspto-grants-2004_10
Patent number
US06809110B2

Linked notes

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