Methyl iodide → HCID 178484001, compound

HRID 1382938Notes

Reaction equation

HRID 1382938 reaction equation
[N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][C:2]=1[C@H:10]1[CH2:15][CH2:14][C@H:13]([CH2:16][N:17]([CH3:28])[C:18](=[O:27])[O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:12][CH2:11]1.[H-].[Na+].[CH3:31]I>CN(C)C=O>[CH3:31][N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C@H:10]1[CH2:15][CH2:14][C@H:13]([CH2:16][N:17]([CH3:28])[C:18](=[O:27])[O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:12][CH2:11]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178484003HCID 178484003, compound

Product 1

HCID 178484001HCID 178484001, compoundYield 79.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 7.2 g (0.019 mol) of benzyl [[trans-4-(2-benzimidazolyl)cyclohexyl]methyl]methylcarbamate in 160 ml of dimethylformamide is treated at 15°-20° under argon with 0.023 mol of sodium hydride (1.0 g of a 55% dispersion in mineral oil) and thereupon stirred at room temperature for a further 30 minutes. A solution of 2.3 ml (0.038 mol) of methyl iodide in 10 ml of dimethylformamide is added thereto at 15°-20° within 15 minutes and the mixture is stirred at room temperature for a further 3 hours. After concentration under reduced pressure the residue is partitioned between ice-water and ethyl acetate. The organic phase, dried over sodium sulphate, is evaporated and the solid residue is recrystallized from ethyl acetate/ether. There are obtained 5.9 g (79%) of benzyl [[trans-4-(1-methyl-2-benzimidazolyl)cyclohexyl]methyl]methylcarbamate, m.p. 141°-142°, as a colourless crystalline powder.

Workup

  1. waitat 15°-20° within 15 minutes
  2. stirringthe mixture is stirred at room temperature for a further 3 hours
  3. concentrationAfter concentration under reduced pressure the residue
  4. customis partitioned between ice-water and ethyl acetate
  5. dry with materialThe organic phase, dried over sodium sulphate
  6. customis evaporated
  7. customthe solid residue is recrystallized from ethyl acetate/ether

Sources & evidence

ORD record
ord-76efc15387ce498099914461573029fd
Source dataset
uspto-grants-1989_02
Patent number
US04808605

Reaction notes

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