Methanol → 4-Cyanomethyl-2-fluoro-1-triphenylmethylimidazole

HRID 2412496Notes

Reaction equation

HRID 2412496 reaction equation
C1(C)C=CC(S([CH2:10][N+:11]#[C-])(=O)=O)=CC=1.CC(C)([O-])C.[K+].[F:20][C:21]1[N:22]([C:28]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:23]=[C:24]([CH:26]=O)[N:25]=1.CO>C(COC)OC.C1COCC1>[C:10]([CH2:26][C:24]1[N:25]=[C:21]([F:20])[N:22]([C:28]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:23]=1)#[N:11]

Participants

7

Reactant 4

HCID 887MethanolHCID 161915Tosylmethyl isocyanideHCID 23665647Potassium tert-butoxideHCID 537790282-Fluoro-1-trityl-1H-imidazole-4-carbaldehyde

Product 1

HCID 204323714-Cyanomethyl-2-fluoro-1-triphenylmethylimidazole

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 80711,2-DimethoxyethaneSolvent2×

Procedure

Examples 44, 45: Toluene-p-sulphonylmethyl isocyanide, dissolved in dimethoxyethane, was added to a suspension of potassium t-butoxide in the same solvent at -30°. The mixture was cooled to -50° and treated with a solution of 2-fluoro-4-formyl-1-triphenylmethylimidazole in THF plus dimethoxyethane. After 45 minutes, MeOH was added and the mixture heated under reflux briefly. Extractive work-up gave 4-cyanomethyl-2-fluoro-1-triphenylmethylimidazole, having the following n.m.r. spectrum in CDCl3 : 3.53 (s, 2H); 6.57 (s, 1H); 7.05-7.45 (m, 15H).

Workup

  1. temperatureThe mixture was cooled to -50°
  2. temperaturethe mixture heated
  3. temperatureunder reflux briefly

Sources & evidence

ORD record
ord-86fdfb5605f141c4a03f0b188a9cb941
Source dataset
uspto-grants-1985_01
Patent number
US04492692

Reaction notes

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