Hydrochloric Acid → HCID 14722382, compound

HRID 1031698Notes

Reaction equation

HRID 1031698 reaction equation
[NH2:1][C:2]1[C:7](=[O:8])[C:6]2[CH:9]=[C:10]([O:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:11]([NH:13][S:14]([CH3:17])(=[O:16])=[O:15])=[CH:12][C:5]=2[O:4][CH:3]=1.N1C=CC=CC=1.[C:31](Cl)(=[O:34])[O:32][CH3:33].Cl>C(Cl)Cl.O>[CH3:33][O:32][C:31]([NH:1][C:2]1[C:7](=[O:8])[C:6]2[CH:9]=[C:10]([O:18][C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:11]([NH:13][S:14]([CH3:17])(=[O:15])=[O:16])=[CH:12][C:5]=2[O:4][CH:3]=1)=[O:34]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 6586Methyl chloroformateHCID 10783765HCID 10783765, compound

Product 1

HCID 14722382HCID 14722382, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To 70 ml of methylene chloride was added 3.46 g of 3-amino-7-methylsulfonylamino-6-phenoxy-4H-1-benzopyran-4-one. Further, 870 mg of pyridine was added thereto. The mixture was ice-cooled. To this solution was dropwise added a solution of 1.04 g of methyl chlorocarbonate dissolved in 30 ml of methylene chloride, in 10 minutes. The mixture was then stirred for 30 minutes at 20°-25° C. 50 ml of water was added thereto. The resulting mixture was adjusted to pH 4 with 4N hydrochloric acid. The organic layer was separated, washed with water and a saturated aqueous sodium chloride solution in this order, and dried with anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The resulting crystal was recrystallized from acetonitrile to obtain 2.95 g (yield: 73%) of 3-methoxycarbonylamino-7-methylsulfonylamino-6-phenoxy-4H-1-benzopyran-4-one having a melting point of 233°-235° C.

Workup

  1. temperaturecooled
  2. customThe organic layer was separated
  3. washwashed with water
  4. dry with materiala saturated aqueous sodium chloride solution in this order, and dried with anhydrous magnesium sulfate
  5. customThe solvent was removed by distillation under reduced pressure
  6. customThe resulting crystal was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-62a1ac4f24e847ed864711dea4358a2d
Source dataset
uspto-grants-1990_09
Patent number
US04954518

Reaction notes

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