Ammonia → HCID 19981882, compound

HRID 1460468Notes

Reaction equation

HRID 1460468 reaction equation
[CH3:1][C:2]1[C:3]([CH3:16])=[CH:4][C:5]2[CH:10]([C:11](O)=[O:12])[S:9][CH2:8][C:7](=[O:14])[C:6]=2[CH:15]=1.C(Cl)(=O)C(Cl)=O.[NH3:23].C(OCC)(=O)C>C1COCC1.CN(C=O)C>[CH3:1][C:2]1[C:3]([CH3:16])=[CH:4][C:5]2[CH:10]([C:11]([NH2:23])=[O:12])[S:9][CH2:8][C:7](=[O:14])[C:6]=2[CH:15]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 8857Ethyl AcetateHCID 65578Oxalyl chlorideHCID 106812951H-2-Benzothiopyran-1-carboxylicacid, 3,4-dihydro-6,7-dimethyl-4-oxo-

Product 1

HCID 19981882HCID 19981882, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

In THF (10 ml) was dissolved 6,7-dimethyl3,4-dihydro-1H-2-benzothiopyran-4-one-1-carboxylic acid (0.473 g) followed by addition of oxalyl chloride (0.305 g) and, then, DMF (1 drop). The mixture was stirred at room temperature for 2 hours. This reaction mixture was added to aqueous ammonia (20 ml)--ethyl acetate (40 ml) and the whole mixture was stirred at room temperature for 30 minutes. The ethyl acetate layer was then separated, washed with water, dried (MgSO4) and the solvent was distilled off to give 6,7-dimethyl-3,4-dihydro-1H-2-benzothiopyran-4-one-1-carboxamide (0.38 g, 81%). Recrystallization from ethyl acetate gave colorless plates melting at 197°-198° C.

Workup

  1. customThe ethyl acetate layer was then separated
  2. washwashed with water
  3. dry with materialdried (MgSO4)
  4. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-affbcde8952f4d48939d42b7064b7f99
Source dataset
uspto-grants-1991_12
Patent number
US05071841

Reaction notes

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