Water → HCID 21254707, compound

HRID 636506Notes

Reaction equation

HRID 636506 reaction equation
[CH2:1]([O:8][C:9]1[C:17]2[N:16]=[C:15](SC)[N:14]([CH2:20][CH2:21][CH2:22][OH:23])[C:13]=2[CH:12]=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].O>CN(C)C=O>[CH2:1]([O:8][C:9]1[C:17]2[N:16]=[C:15]3[O:23][CH2:22][CH2:21][CH2:20][N:14]3[C:13]=2[CH:12]=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24758Sodium hydrideHCID 21254675HCID 21254675, compound

Product 1

HCID 21254707HCID 21254707, compoundYield 85.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-benzyloxy-1-(3-hydroxypropyl)-2-methylthio-1H-benzimidazole (59 mg) in dimethylformamide (1 ml) was added sodium hydride at ambient temperature, and the mixture was stirred overnight. Water was added to the reaction mixture, and extracted with ethyl acetate. The extract was washed with water and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by preparative thin layer chromatography (chloroform:methanol=10:1, v/v) and pulverized with diisopropyl ether to give 9-benzyloxy-3,4-dihydro-2H-[1,3]oxazino-[3,2-a]benzimidazole (43 mg).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was purified by preparative thin layer chromatography (chloroform

Sources & evidence

ORD record
ord-e24b354d4d8c40c4afaa2564dee95c67
Source dataset
uspto-grants-2001_02
Patent number
US06194396B1

Reaction notes

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