Hydrochloric Acid → HCID 10783765, compound

HRID 1031713Notes

Reaction equation

HRID 1031713 reaction equation
Br[CH: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][CH2:3]1.[N-:25]=[N+]=[N-].[Na+].O.Cl>CN(C)C=O.C(OCC)(=O)C>[NH2:25][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

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 33557Sodium AzideHCID 10621601HCID 10621601, compound

Product 1

HCID 10783765HCID 10783765, compoundYield 82.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

In 280 ml of N,N-dimethylformamide was dissolved 40.1 g of 3-bromo-2,3-dihydro-7-methylsulfonylamino-6-phenoxy-4H-1-benzopyran-4-one. Thereto was added 13.9 g of sodium azide. The mixture was stirred for 1 hour at 70°-75° C. The reaction mixture was introduced into a mixed solvent consisting of 1.5 liters of water and 300 ml of ethyl acetate. The mixture was adjusted to pH 0.1 with conc. hydrochloric acid. The aqueous layer was separated, washed with 200 ml of ethyl acetate, adjusted to pH 4.0 with a 10% aqueous sodium hydroxide solution, and extracted with two 500-ml portions of ethyl acetate. The extracts (the organic layers) were combined, 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 crystal was recrystallized from ethanol to obtain 2.84 g (yield: 82.1%) of 3-amino-7-methylsulfonylamino-6-phenoxy-4H-1 -benzopyran-4-one having a melting point of 162°-163° C.

Workup

  1. additionThe reaction mixture was introduced into a mixed solvent
  2. customThe aqueous layer was separated
  3. washwashed with 200 ml of ethyl acetate
  4. extractionextracted with two 500-ml portions of ethyl acetate
  5. washwashed with water
  6. dry with materiala saturated aqueous sodium chloride solution in this order, and dried with anhydrous magnesium sulfate
  7. customThe solvent was removed by distillation under reduced pressure
  8. customThe crystal was recrystallized from ethanol

Sources & evidence

ORD record
ord-567ff668431a47a3ba8b8b66531c11ef
Source dataset
uspto-grants-1990_09
Patent number
US04954518

Reaction notes

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