Glycol monoacetate → 2-(4-(2-acetoxyethyloxy)phenyl)-5-(4-chlorophenyl)-N-(2-thiazolyl)imidazole-4-carboxamide

HRID 1595434Notes

Reaction equation

HRID 1595434 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:12][C:11]([C:13]3[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=3)=[N:10][C:9]=2[C:20]([NH:22][C:23]2[S:24][CH:25]=[CH:26][N:27]=2)=[O:21])=[CH:4][CH:3]=1.[C:28]([O:31][CH2:32][CH2:33]O)(=[O:30])[CH3:29].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>>[C:28]([O:31][CH2:32][CH2:33][O:19][C:16]1[CH:17]=[CH:18][C:13]([C:11]2[NH:12][C:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)=[C:9]([C:20]([NH:22][C:23]3[S:24][CH:25]=[CH:26][N:27]=3)=[O:21])[N:10]=2)=[CH:14][CH:15]=1)(=[O:30])[CH3:29]

Participants

5

Reactant 4

HCID 10960Glycol monoacetateHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 1785225775-(4-Chlorophenyl)-2-(4-hydroxyphenyl)-N-(2-thiazolyl)-imidazole-4-carboxamide

Product 1

HCID 1784764282-(4-(2-acetoxyethyloxy)phenyl)-5-(4-chlorophenyl)-N-(2-thiazolyl)imidazole-4-carboxamide

Procedure

5-(4-Chlorophenyl)-2-(4-hydroxyphenyl)-N-(2-thiazolyl)-imidazole-4-carboxamide, 2-hydroxyethyl acetate, triphenylphosphine and diethyl azodicarboxylate are reacted and treated in the same manner as in Example 24 to give 2-(4-(2-acetoxyethyloxy)phenyl)-5-(4-chlorophenyl)-N-(2-thiazolyl)imidazole-4-carboxamide.

Workup

  1. additiontreated in the same manner as in Example 24

Sources & evidence

ORD record
ord-da80250460bc4510b96eb5ef2136d111
Source dataset
uspto-grants-2001_09
Patent number
US06288061B1

Reaction notes

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