Hydrochloric Acid → HCID 14722417, compound

HRID 1031689Notes

Reaction equation

HRID 1031689 reaction equation
O[C:2]1[O:3][C:4]2[CH:15]=[C:14]([NH:16][S:17]([CH3:20])(=[O:19])=[O:18])[C:13]([O:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:12][C:5]=2[C:6](=[O:11])[C:7]=1[N+:8]([O-:10])=[O:9].[OH-].[Na+].Cl>C(OCC)(=O)C>[N+:8]([C:7]1[C:6](=[O:11])[C:5]2[CH:12]=[C:13]([O:21][C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:14]([NH:16][S:17]([CH3:20])(=[O:19])=[O:18])=[CH:15][C:4]=2[O:3][CH:2]=1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 178504978HCID 178504978, compound

Product 1

HCID 14722417HCID 14722417, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

3.92 g of 2-hydroxy-7-methylsulfonylamino-3-nitro-6-phenoxy-4H-1-benzopyran-4-one was mixed with 80 ml of a 1N aqueous sodium hydroxide solution. The mixture was stirred for 5 hours at 20°-25° C. The mixture was adjusted to pH 5 with 4N hydrochloric acid. 50 ml of ethyl acetate was added thereto. 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 yellow solid was dissolved in N,N-dimethylformamide. 2.62 g of N,N-dimethylformamide dimethylacetal was added thereto. The mixture was stirred for 1 hour at 20°-25° C. The reaction mixture was introduced into 300 ml of water. The resulting mixture was adjusted to pH 2 with 4N hydrochloric acid. The precipitate was washed with water and then recrystallized from acetonitrile to obtain 1.54 g (yield: 41%) of 3-nitro-7-methylsulfonylamino-6-phenoxy-4H-1-benzopyran-4-one having a melting point of 225°-227° C.

Workup

  1. customThe organic layer was separated
  2. washwashed with water
  3. dry with materiala saturated aqueous sodium chloride solution in this order, and dried with anhydrous magnesium sulfate
  4. customThe solvent was removed by distillation under reduced pressure
  5. dissolutionThe resulting yellow solid was dissolved in N,N-dimethylformamide
  6. addition2.62 g of N,N-dimethylformamide dimethylacetal was added
  7. stirringThe mixture was stirred for 1 hour at 20°-25° C
  8. additionThe reaction mixture was introduced into 300 ml of water
  9. washThe precipitate was washed with water
  10. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-f5def10b9d0f480f97302d9adcabd0e8
Source dataset
uspto-grants-1990_09
Patent number
US04954518

Reaction notes

Loading…