Water → HCID 59749210, compound

HRID 896616Notes

Reaction equation

HRID 896616 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH2:20][CH2:21][CH2:22][NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[C:10](=[N:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[S:11][CH:12]=2)=[CH:4][CH:3]=1.[H-].[Na+].[CH3:33]I.O>CN(C)C=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH2:20][CH2:21][CH2:22][N:23]([CH3:33])[C:24](=[O:30])[O:25][C:26]([CH3:27])([CH3:29])[CH3:28])[C:10](=[N:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[S:11][CH:12]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 22350984HCID 22350984, compound

Product 1

HCID 59749210HCID 59749210, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

t-Butyl 3-[4-(4-bromophenyl)-2-(phenylimino)thiazol-3(2H)-yl]propylcarbamate (250 mg) was dissolved in N,N-dimethylformamide (2 ml), and thereto was added sodium hydride (26 mg, 60% dispersion in oil) under nitrogen atmosphere in an ice bath, and the mixture was stirred for 15 minutes. To the reaction mixture was added methyl iodide (41 μl), and the mixture was warmed to room temperature, and stirred for 6 hours. Water was added to the reaction mixture, and the mixture was extracted with diethyl ether. The organic layer was washed with a saturated brine, dried over sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography [n-hexane:ethyl acetate (10:1)] to give the title compound (249 mg) as colorless oil.

Workup

  1. stirringstirred for 6 hours
  2. extractionthe mixture was extracted with diethyl ether
  3. washThe organic layer was washed with a saturated brine
  4. dry with materialdried over sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography [n-hexane:ethyl acetate (10:1)]

Sources & evidence

ORD record
ord-3e19a903dca84153a9bd3744fd4a4b6a
Source dataset
uspto-grants-2005_07
Patent number
US06919361B2

Reaction notes

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