Phenyl isocyanate → 2-Fluoro-4-phenylcarbamoyl-1-triphenylmethylimidazole

HRID 2412509Notes

Reaction equation

[F:1][C:2]1[N:3]([C:7]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:4]=[CH:5][N:6]=1.C([Li])CCC.[C:31]1([N:37]=[C:38]=[O:39])[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>>[F:1][C:2]1[N:3]([C:7]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:4]=[C:5]([C:38](=[O:39])[NH:37][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[N:6]=1

Participants

Reactant 3

HCID 7672Phenyl isocyanate

HCID 204324542-Fluoro-1-trityl-1H-imidazole

HCID 178418339Butyllithium

Product 1

HCID 204324322-Fluoro-4-phenylcarbamoyl-1-triphenylmethylimidazole

Procedure

Reaction of 2-fluoro-1-triphenylmethylimidazole with n-butyl lithium at -75° followed by treatment with phenylisocyanate gave 2-fluoro-4-phenylcarbamoyl-1-triphenylmethylimidazole, n.m.r. in CDCl3 : 7.0-7.5 (m, 19H); 7.6 (d, 2H); 8.6 (s, 1H). Reaction of this product with toluene-p-sulphonic acid in DMF at 85° for 15 minutes gave 2-fluoro-4-phenylcarbamoylimidazole, n.m.r. in CDCl3 : 6.9-8.0 (m, 6H); 9.6 (s, 1H).

Sources & evidence

ORD record: ord-3a03abae24b643eaac40171be917a124
Source dataset: uspto-grants-1985_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04492692

Reaction notes

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