Sodium Cyanide → 4-(1-Dimethylaminocyanomethyl)-2-fluoro-1-triphenylmethylimidazole

HRID 2412508Notes

Reaction equation

HRID 2412508 reaction equation
Cl.[CH3:2][NH:3][CH3:4].[C-:5]#[N:6].[Na+].[F:8][C:9]1[N:10]([C:16]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:11]=[C:12]([CH:14]=O)[N:13]=1>C1COCC1>[CH3:2][N:3]([CH3:4])[CH:14]([C:5]#[N:6])[C:12]1[N:13]=[C:9]([F:8])[N:10]([C:16]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:11]=1

Participants

5

Reactant 3

HCID 8929Sodium CyanideHCID 10473Dimethylamine, hydrochlorideHCID 537790282-Fluoro-1-trityl-1H-imidazole-4-carbaldehyde

Product 1

HCID 204323644-(1-Dimethylaminocyanomethyl)-2-fluoro-1-triphenylmethylimidazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

An aqueous solution of dimethylamine hydrochloride and NaCN was added to a solution of 2-fluoro-4-formyl-1-triphenylmethylimidazole in THF. After stirring 3 hours at 20°, work-up gave 4-(1-dimethylaminocyanomethyl)-2-fluoro-1-triphenylmethylimidazole having the following n.m.r. in CDCl3 : 2.31 (s, 6H); 4.64 (s, 1H); 6.68 (s, 1H); 7.04-7.45 (m, 15H).

Sources & evidence

ORD record
ord-040ffee1a39b40b99d55380c0c2d70d4
Source dataset
uspto-grants-1985_01
Patent number
US04492692

Reaction notes

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