Water → HCID 15290092, compound

HRID 1440241Notes

Reaction equation

HRID 1440241 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7]Cl)=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].[OH:17][CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][C:19]1([N:28]1[CH:32]=[C:31]([N+:33]([O-:35])=[O:34])[N:30]=[CH:29]1)[C:24](=[S:27])[NH:25][CH3:26].O>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][S:27][C:24](=[N:25][CH3:26])[C:19]2([N:28]3[CH:32]=[C:31]([N+:33]([O-:35])=[O:34])[N:30]=[CH:29]3)[CH2:20][CH2:21][CH2:22][CH2:23][CH:18]2[OH:17])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 699934-Methyloxybenzyl chlorideHCID 19973447HCID 19973447, compound

Product 1

HCID 15290092HCID 15290092, compoundYield 66.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

21.7 ml (160 mmol) of 4-methoxybenzyl chloride and 32.94 g (238 mmol) of potassium carbonate were added to a solution of 45.23 g (159 mmol) of the 2-hydroxy-N-methyl-1-(4-nitroimidazol-1-yl)cyclohexanecarbothioamide (L form) prepared in the Example 17 in 300 ml of N,N-dimethylformamide. The obtained mixture was stirred at room temperature for 17 hours to give a yellowish-brown suspension. Water and common salt were added to this suspension and the obtained mixture was extracted with ethyl acetate. The organic phase was washed with a saturated aqueous solution of common salt, dried over anhydrous magnesium sulfate, and concentrated in a vacuum. The obtained residue (65.5 g) was recrystallized from dichloromethane/ethyl acetate to give 42.78 g of the title compound as a light yellowish-brown crystal (yield: 66%).

Workup

  1. customto give a yellowish-brown suspension
  2. extractionthe obtained mixture was extracted with ethyl acetate
  3. washThe organic phase was washed with a saturated aqueous solution of common salt
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in a vacuum
  6. customThe obtained residue (65.5 g) was recrystallized from dichloromethane/ethyl acetate

Sources & evidence

ORD record
ord-4da7bbfbc9844a1b96d4cb2551a17dfe
Source dataset
uspto-grants-1996_03
Patent number
US05498634

Reaction notes

Loading…