Sodium hydride → HCID 13363535, compound

HRID 1788943Notes

Reaction equation

HRID 1788943 reaction equation
[H-].[Na+].[CH2:3]([O:5][C:6]1[C:11]2[O:12][CH2:13][O:14][CH2:15][C:10]=2[CH:9]=[C:8]([NH:16][C:17](=[O:22])[O:18][CH:19]([CH3:21])[CH3:20])[CH:7]=1)[CH3:4].[C:23]1([S:29]Cl)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CN(C)C=O>[C:23]1([S:29][N:16]([C:8]2[CH:7]=[C:6]([O:5][CH2:3][CH3:4])[C:11]3[O:12][CH2:13][O:14][CH2:15][C:10]=3[CH:9]=2)[C:17](=[O:22])[O:18][CH:19]([CH3:21])[CH3:20])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 11008040Benzenesulfenyl chlorideHCID 13363515HCID 13363515, compound

Product 1

HCID 13363535HCID 13363535, compoundYield 87.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (0.107 g; 60% dispersion in mineral oil) was dispersed in N,N-dimethylformamide (20 ml). To this solution was added isopropyl N-(8-ethoxy-1,3-benzodioxan-6-yl)carbamate (0.75 g) under ice-cooling. After being stirred at room temperature for 1 hour, phenylsulfenyl chloride (0.39 g) was added thereto under ice-cooling, and stirring was continued at room temperature overnight. The resulting mixture was poured into ice-water and extracted with ethyl acetate. The extract was washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography using a mixture of toluene and ethyl acetate as the eluent to give isopropyl N-phenylthio-N-(8-ethoxy-1,3-benzodioxan-6-yl)carbamate (Compound 25) (0.91 g) in a yield of 87.5%. M.P., 120°-123° C.

Workup

  1. temperaturecooling
  2. temperatureunder ice-cooling
  3. stirringstirring
  4. waitwas continued at room temperature overnight
  5. extractionextracted with ethyl acetate
  6. washThe extract was washed with water
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel chromatography
  10. additiona mixture of toluene and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-323422090e9547dfb62757ce11acaab4
Source dataset
uspto-grants-1987_08
Patent number
US04686232

Reaction notes

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