Hydrochloric Acid → HCID 14722383, compound

HRID 1031714Notes

Reaction equation

HRID 1031714 reaction equation
[Br:1][C:2]1(Br)[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.O.Cl>N1C=CC=CC=1>[Br: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

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 22168209HCID 22168209, compound

Product 1

HCID 14722383HCID 14722383, compoundYield 82.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In 20 ml of pyridine was dissolved 4.81 g of 3,3-dibromo-2,3-dihydro-7-methylsulfonylamino-6phenoxy-4H-1-benzopyran-4-one. The solution was refluxed for 20 minutes. The reaction mixture was introduced into 200 ml of water. The mixture was adjusted to pH 4 with concentrated hydrochloric acid and then extracted with two 100-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 resulting crystal was recrystallized from acetonitrile to obtain 3.30 g (yield: 82%) of 3-bromo-7-methylsulfonylamino-6-phenoxy-4H-1-benzopyran-4-one having a melting point of 215°-216° C.

Workup

  1. temperatureThe solution was refluxed for 20 minutes
  2. extractionextracted with two 100-ml portions of ethyl acetate
  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-9eafcfcd70854aac83658c18336f1968
Source dataset
uspto-grants-1990_09
Patent number
US04954518

Reaction notes

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