Trifluoroacetic acid → Methyl-phenyl-carbamic Acid 4-(imidazol-1-yloxymethyl)-phenyl Ester

HRID 1831428Notes

Reaction equation

HRID 1831428 reaction equation
C(O)(C(F)(F)F)=O.[OH:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17](=[O:26])[N:18]([CH3:25])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:12][CH:11]=1.Cl.O[N:29]1[CH:33]=[CH:32][N:31]=[CH:30]1>>[N:29]1([O:8][CH2:9][C:10]2[CH:11]=[CH:12][C:13]([O:16][C:17](=[O:26])[N:18]([CH3:25])[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)=[CH:14][CH:15]=2)[CH:33]=[CH:32][N:31]=[CH:30]1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 103131281-hydroxyimidazole HydrochlorideHCID 69518671Methyl-phenyl-carbamic Acid 4-hydroxymethyl-phenyl Ester

Product 1

HCID 69519595Methyl-phenyl-carbamic Acid 4-(imidazol-1-yloxymethyl)-phenyl EsterYield 87%

Procedure

The title compound was prepared as its TFA salt in 87% yield as a solid using methyl-phenyl-carbamic acid 4-hydroxymethyl-phenyl ester and 1-hydroxyimidazole, hydrochloride. 1H NMR (400 MHz; CDCl3): δ 3.42 (br s, 3H), 5.21 (s, 2H), 6.95 (s, 1H), 7.16–7.45 (m, 10H) 8.28 (br s, 1H); HPLC-MS: m/z=324.1 (M+1); Rt=1.92 min.

Sources & evidence

ORD record
ord-ce03c18783d844a8b3baa02d0d7943a3
Source dataset
uspto-grants-2006_06
Patent number
US07067517B2

Reaction notes

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