4H-1-Benzopyran-2-carboxylic acid, 4-oxo-, methyl ester → HCID 85040445, compound

HRID 1378338Notes

Reaction equation

HRID 1378338 reaction equation
[CH3:1][O:2][C:3]([C:5]1[O:6][C:7]2[C:12]([C:13](=O)[CH:14]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2)=[O:4].[C:16]1([S:22]([N:25]=C=O)(=[O:24])=[O:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(#N)C>[C:16]1([S:22]([N:25]=[C:13]2[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[O:6][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:14]2)(=[O:24])=[O:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 290574H-1-Benzopyran-2-carboxylic acid, 4-oxo-, methyl esterHCID 76096Phenylsulphonyl isocyanate

Product 1

HCID 85040445HCID 85040445, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Combine chromone-2-carboxylic acid methyl ester (0.341 g, 1.66 mmol) and benzenesulfonyl isocyanate (0.365 g, 1.88 mmol) in acetonitrile (5.0 mL) and reflux. After 24 hours, quench the reaction with methanol (1 mL). Concentrate in vacuo and triturate with hexane. Filter to obtain a paste. Recrystallize the paste from methanol to obtain a solid. Recrystallize from methanol to give the title compound as a solid: mp; 144°-146° C.

Workup

  1. customquench
  2. customthe reaction with methanol (1 mL)
  3. concentrationConcentrate in vacuo
  4. customtriturate with hexane
  5. filtrationFilter
  6. customto obtain a paste
  7. customRecrystallize the paste from methanol
  8. customto obtain a solid
  9. customRecrystallize from methanol

Sources & evidence

ORD record
ord-15b1a1b0835442649abd6df46531193e
Source dataset
uspto-grants-1997_09
Patent number
US05668143

Reaction notes

Loading…