Sodium hydride → HCID 19981883, compound

HRID 1460467Notes

Reaction equation

HRID 1460467 reaction equation
[CH3:1][C:2]1[C:3]([CH3:16])=[CH:4][C:5]2[CH:10]([C:11]([OH:13])=O)[S:9][CH2:8][C:7](=[O:14])[C:6]=2[CH:15]=1.C(Cl)(=O)C(Cl)=O.[CH2:23]([O:25][P:26]([NH2:31])([O:28][CH2:29][CH3:30])=[O:27])[CH3:24].[H-].[Na+]>C1COCC1.CN(C=O)C.O>[CH2:23]([O:25][P:26]([NH:31][C:11]([CH:10]1[C:5]2[CH:4]=[C:3]([CH3:16])[C:2]([CH3:1])=[CH:15][C:6]=2[C:7](=[O:14])[CH2:8][S:9]1)=[O:13])([O:28][CH2:29][CH3:30])=[O:27])[CH3:24]

Participants

8

Reactant 4

HCID 24758Sodium hydrideHCID 65578Oxalyl chlorideHCID 70605Phosphoramidic acid, diethyl ester (8CI)(9CI)HCID 106812951H-2-Benzothiopyran-1-carboxylicacid, 3,4-dihydro-6,7-dimethyl-4-oxo-

Product 1

HCID 19981883HCID 19981883, compoundYield 19.5%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 6,7-dimethyl-3,4-dihydro-1H-2-benzothiopyran-4-one-1-carboxylic acid (0.945 g) in THF (10 ml) were added oxalyl chloride (0.609 g) and DMF (2 drops), and the mixture was stirred at room temperature for 1 hour. On the other hand, a mixture of diethoxyphosphorylamine (4.9 g), sodium hydride in oil (60%, 0.32 g) and THF (30 ml) was stirred with ice-cooling for 30 minutes and, then, the above solution was added. The mixture was stirred with ice-cooling for 30 minutes, poured into water and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4) and the solvent was distilled off to give N-diethoxyphosphoryl-6,7-dimethyl-3,4-dihydro-1H-2-benzothiopyran-4-one-1-carboxamide (0.29 g, 19%). Recrystallization from ethyl acetate gave colorless prisms melting at 192°-1931/2° C.

Workup

  1. stirringwas stirred with ice-
  2. temperaturecooling for 30 minutes
  3. additionthe above solution was added
  4. stirringThe mixture was stirred with ice-
  5. temperaturecooling for 30 minutes
  6. extractionextracted with ethyl acetate
  7. washThe ethyl acetate layer was washed with water
  8. dry with materialdried (MgSO4)
  9. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-5036b924b6ec44629c4ba7256717d8e9
Source dataset
uspto-grants-1991_12
Patent number
US05071841

Reaction notes

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