Diethyl Ether → 2-Fluoro-4-methylthio-1-triphenylmethylimidazole

HRID 2412472Notes

Reaction equation

HRID 2412472 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])(C)(C)C.[CH3:31][S:32]SC.CCOCC>CCCCC.C1COCC1>[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]([S:32][CH3:31])[N:6]=1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 12232Dimethyl DisulfideHCID 204324542-Fluoro-1-trityl-1H-imidazoleHCID 178418306HCID 178418306, compound

Product 1

HCID 130937732-Fluoro-4-methylthio-1-triphenylmethylimidazole

Reagents, catalysts & solvents 2

HCID 8003PentaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-fluoro-1-triphenylmethylimidazole (0.328 g.) and t-butyl lithium (1.0 ml. of a 2M solution in pentane) in THF (3 ml.) was stirred at -78° for 2 hours. Dimethyl disulphide (0.18 ml.) was added and the mixture was stirred for 0.5 hours at -78° then at -15° for 1 hour. Ether was added and the organic layer washed to neutrality with water and finally with brine. The solution was dried and the solvent evaporated to give 2-fluoro-4-methylthio-1-triphenylmethylimidazole (0.368 g.), m.p. 142°-143°.

Workup

  1. waitat -15° for 1 hour
  2. washthe organic layer washed
  3. customThe solution was dried
  4. customthe solvent evaporated

Sources & evidence

ORD record
ord-579296b120f64d8fa3db40ea9db776e8
Source dataset
uspto-grants-1985_01
Patent number
US04492692

Reaction notes

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