Methanol → HCID 14722391, compound

HRID 1031700Notes

Reaction equation

HRID 1031700 reaction equation
[Na].Br[C:3]1[O:4][C:5]2[CH:16]=[C:15]([NH:17][S:18]([CH3:21])(=[O:20])=[O:19])[C:14]([O:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:13][C:6]=2[C:7](=[O:12])[C:8]=1[NH:9][CH:10]=[O:11].[OH2:29].[CH3:30]O>>[CH:10]([NH:9][C:8]1[C:7](=[O:12])[C:6]2[CH:13]=[C:14]([O:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:15]([NH:17][S:18]([CH3:21])(=[O:20])=[O:19])=[CH:16][C:5]=2[O:4][C:3]=1[O:29][CH3:30])=[O:11]

Participants

5

Reactant 4

HCID 887MethanolHCID 962WaterHCID 5360545SodiumHCID 14722390HCID 14722390, compound

Product 1

HCID 14722391HCID 14722391, compoundYield 71%

Procedure

510 mg of metallic sodium was dissolved in 60 ml of methanol. The solution was ice-cooled. Thereto was added 4.25 g of 2-bromo-3-formylamino-7-methylsulfonylamino-6-phenoxy-4H-1-benzopyran-4-one. The mixture was stirred for 2 hours at 0°-5° C. 600 ml of water was added thereto. The resulting mixture was washed with 200 ml of ethyl acetate, adjusted to pH 4 with 4N hydrochloric acid, and extracted with two 300-ml portions of ethyl acetate. The extracts (the organic layers) were combined, washed with a saturated aqueous sodium chloride solution, and dried with anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The resulting crystal was recrystallized from acetonitrile to obtain 2.87 g (yield: 71%) of 3-formylamino-2-methoxy-7-methylsulfonylamino-6-phenoxy-4H-1-benzopyran-4-one having a melting point of 188° C. (decomposed).

Workup

  1. temperaturecooled
  2. washThe resulting mixture was washed with 200 ml of ethyl acetate
  3. extractionextracted with two 300-ml portions of ethyl acetate
  4. washwashed with a saturated aqueous sodium chloride solution
  5. dry with materialdried with anhydrous magnesium sulfate
  6. customThe solvent was removed by distillation under reduced pressure
  7. customThe resulting crystal was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-dfdbaa918dd44d229626a00c30b019a1
Source dataset
uspto-grants-1990_09
Patent number
US04954518

Reaction notes

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