Sodium hydride → HCID 14722437, compound

HRID 1031691Notes

Reaction equation

HRID 1031691 reaction equation
[C:1]([NH:4][C:5]1[C:15]([O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:14][C:8]2[C:9](=[O:13])[CH:10]=[CH:11][O:12][C:7]=2[CH:6]=1)(=[O:3])[CH3:2].[H-].[Na+].[H][H].[CH3:27][S:28](Cl)(=[O:30])=[O:29]>CN(C)C=O.C(OCC)(=O)C.O>[C:1]([N:4]([C:5]1[C:15]([O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:14][C:8]2[C:9](=[O:13])[CH:10]=[CH:11][O:12][C:7]=2[CH:6]=1)[S:28]([CH3:27])(=[O:30])=[O:29])(=[O:3])[CH3:2]

Participants

8

Reactant 4

HCID 24758Sodium hydrideHCID 31297Methanesulfonyl chlorideHCID 22168210HCID 22168210, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 14722437HCID 14722437, compoundYield 86.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

2.95 g of 7-acetylamino-6-phenoxy-4H-1-benzopyran-4-one was dissolved in 30 ml of N,N-dimethylformamide. 440 mg of sodium hydride (purity: 60%) was added thereto with ice-cooling. The mixture was stirred at the same temperature until the generation of hydrogen gas stopped. Then, 1.26 g of methanesulfonyl chloride was added thereto dropwise. The mixture was stirred for 1 hour at 20°-25° C. 200 ml of water and 200 ml of ethyl acetate were added thereto. The organic layer was separated, washed with water and a saturated aqueous sodium chloride solution in this order, and dried with anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The resulting crystal was recrystallized from ethanol to obtain 3.22 g (yield: 86.1%) of 7-(N-acetyl-N-methylsulfonylamino)-6-phenoxy-4H-1-benzopyran-4-one having a melting point of 166°-169° C.

Workup

  1. temperaturewith ice-cooling
  2. customThe organic layer was separated
  3. washwashed with water
  4. dry with materiala saturated aqueous sodium chloride solution in this order, and dried with anhydrous magnesium sulfate
  5. customThe solvent was removed by distillation under reduced pressure
  6. customThe resulting crystal was recrystallized from ethanol

Sources & evidence

ORD record
ord-6a8f00b3499a466285466ed48aafb8ac
Source dataset
uspto-grants-1990_09
Patent number
US04954518

Reaction notes

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