Hydrochloric Acid → HCID 14722380, compound

HRID 1031715Notes

Reaction equation

HRID 1031715 reaction equation
[CH3:1][NH2:2].Br[C:4]1[C:9](=[O:10])[C:8]2[CH:11]=[C:12]([O:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:13]([NH:15][S:16]([CH3:19])(=[O:18])=[O:17])=[CH:14][C:7]=2[O:6][CH:5]=1.Cl>O>[CH3:1][NH:2][C:4]1[C:9](=[O:10])[C:8]2[CH:11]=[C:12]([O:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:13]([NH:15][S:16]([CH3:19])(=[O:18])=[O:17])=[CH:14][C:7]=2[O:6][CH:5]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6329MethylamineHCID 14722383HCID 14722383, compound

Product 1

HCID 14722380HCID 14722380, compoundYield 11.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

50 ml of a 25% aqueous methylamine solution was ice-cooled. Thereto was added 4.1 g of 3-bromo-7-methylsulfonylamino-6-phenoxy-4H-1-benzopyran-4-one. The mixture was stirred for 2 hours at 0°-5° C. 100 ml of water was added thereto. The mixture was adjusted to pH 4 with 4N hydrochloric acid and then extracted with 100 ml of ethyl acetate. The extract was washed with a saturated aqueous sodium chloride solution and dried with anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue was purified by a column chromatography (eluant: a 5:1 mixture of toluene and ethyl acetate) and then recrystallized from ethanol to obtain 400 mg (yield: 11.1%) of 3-methylamino-7-methylsulfonylamino-6-phenoxy-4H-1-benzopyran-4-one.

Workup

  1. temperaturecooled
  2. extractionextracted with 100 ml of ethyl acetate
  3. washThe extract was washed with a saturated aqueous sodium chloride solution
  4. dry with materialdried with anhydrous magnesium sulfate
  5. customThe solvent was removed by distillation under reduced pressure
  6. customThe residue was purified by a column chromatography (eluant
  7. additiona 5:1 mixture of toluene and ethyl acetate) and
  8. customthen recrystallized from ethanol

Sources & evidence

ORD record
ord-1747037c4d7840c3b71c7ee93ac43e09
Source dataset
uspto-grants-1990_09
Patent number
US04954518

Reaction notes

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