Hydrochloric Acid → 3-carboxy-7-methylsulfonylamino-6-phenoxy4H-1-benzopyran-4-one

HRID 1031681Notes

Reaction equation

HRID 1031681 reaction equation
O1CCOCC1.Cl.C([O:10][C:11]([C:13]1[C:18](=[O:19])[C:17]2[CH:20]=[C:21]([O:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:22]([NH:24][S:25]([CH3:28])(=[O:27])=[O:26])=[CH:23][C:16]=2[O:15][CH:14]=1)=[O:12])C>O>[C:11]([C:13]1[C:18](=[O:19])[C:17]2[CH:20]=[C:21]([O:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:22]([NH:24][S:25]([CH3:28])(=[O:26])=[O:27])=[CH:23][C:16]=2[O:15][CH:14]=1)([OH:12])=[O:10]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 105491483-ethoxycarbonyl-7-methylsulfonylamino-6-phenoxy-4H-1-benzopyran-4-one

Product 1

HCID 108094623-carboxy-7-methylsulfonylamino-6-phenoxy4H-1-benzopyran-4-oneYield 91%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

80 ml of dioxane and 40 ml of 6N hydrochloric acid were added to 4.03 g of 3-ethoxycarbonyl-7-methylsulfonylamino-6-phenoxy-4H-1-benzopyran-4-one. The mixture was refluxed for 30 minutes. The reaction mixture was cooled. 200 ml of water was added thereto. The resulting crystal was collected by filtration, washed with water and recrystallized from acetic acid to obtain 3.41 g (yield: 91%) of 3-carboxy-7-methylsulfonylamino-6-phenoxy4H-1-benzopyran-4-one having a melting point of >250° C.

Workup

  1. temperatureThe mixture was refluxed for 30 minutes
  2. temperatureThe reaction mixture was cooled
  3. filtrationThe resulting crystal was collected by filtration
  4. washwashed with water
  5. customrecrystallized from acetic acid

Sources & evidence

ORD record
ord-c99cbd1030524defaedb251ca2690f63
Source dataset
uspto-grants-1990_09
Patent number
US04954518

Reaction notes

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