Acetyl isocyanate → 4-(3-Acetylcarbamoyloxypropyl)-2-fluoro-1-triphenylmethylimidazole

HRID 2412477Notes

Reaction equation

HRID 2412477 reaction equation
[F:1][C:2]1[N:3]([C:11]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:4]=[C:5]([CH2:7][CH2:8][CH2:9][OH:10])[N:6]=1.[C:30]([N:33]=[C:34]=[O:35])(=[O:32])[CH3:31].FC1N(C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=C(CCCOC(=O)NC2C=CC=CC=2)N=1>N1C=CC=CC=1>[C:30]([NH:33][C:34]([O:10][CH2:9][CH2:8][CH2:7][C:5]1[N:6]=[C:2]([F:1])[N:3]([C:11]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:4]=1)=[O:35])(=[O:32])[CH3:31]

Participants

5

Reactant 3

HCID 12300404Acetyl isocyanateHCID 204324512-Fluoro-4-(3-phenylcarbamoyloxypropyl)-1-triphenylmethylimidazoleHCID 204324552-Fluoro-4-(3-hydroxypropyl)-1-triphenylmethylimidazole

Product 1

HCID 204324074-(3-Acetylcarbamoyloxypropyl)-2-fluoro-1-triphenylmethylimidazole

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 2-fluoro-4-(3-hydroxypropyl)-1-triphenylmethylimidazole in pyridine was treated with acetyl isocyanate at 85°. Work up as for the starting material of Example 11 gave 4-(3-acetylcarbamoyloxypropyl)-2-fluoro-1-triphenylmethylimidazole, having the following n.m.r. spectrum in d6DMSO: 1.82 (m, 2H); 2.12 (s, 3H); 2.45 (t, 2H) 4.05 (t, 2H); 6.28 (s, 1H); 7.0-7.5 (m, 15H); 10.12 (br, 1H).

Sources & evidence

ORD record
ord-8d8b2b09640c4caea5db66a7a5fdc805
Source dataset
uspto-grants-1985_01
Patent number
US04492692

Reaction notes

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