Methanesulfonyl chloride → HCID 10806538, compound

HRID 1031694Notes

Reaction equation

HRID 1031694 reaction equation
[NH2:1][C:2]1[C:12]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:11][C:5]2[C:6](=[O:10])[CH2:7][CH2:8][O:9][C:4]=2[CH:3]=1.[CH3:20][S:21](Cl)(=[O:23])=[O:22]>N1C=CC=CC=1>[CH3:20][S:21]([NH:1][C:2]1[C:12]([O:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[CH:11][C:5]2[C:6](=[O:10])[CH2:7][CH2:8][O:9][C:4]=2[CH:3]=1)(=[O:23])=[O:22]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 14722314HCID 14722314, compound

Product 1

HCID 10806538HCID 10806538, compoundYield 81.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In 200 ml of pyridine was dissolved 25.5 g of 7-amino-2,3-dihydro-6-phenoxy-4H-1-benzopyran-4-one. To the solution being maintained at 20°-25° C. was dropwise added 12.6 g of methanesulfonyl chloride. The mixture was subjected to reaction for 12 hours at the same temperature. The solvent was removed by distillation under reduced pressure. The residue was dissolved in 200 ml of ethyl acetate. The solution was extracted with two 500-ml portions of a 1N aqueous sodium hydroxide solution. The extracts (the aqueous layers) were combined, 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 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 methanol to obtain 27.0 g (yield: 81.1%) of 2,3-dihydro-7-methylsulfonylamino-6-phenoxy-4H-1-benzopyran-4-one.

Workup

  1. temperatureTo the solution being maintained at 20°-25° C.
  2. customThe mixture was subjected to reaction for 12 hours at the same temperature
  3. customThe solvent was removed by distillation under reduced pressure
  4. dissolutionThe residue was dissolved in 200 ml of ethyl acetate
  5. extractionThe solution was extracted with two 500-ml portions of a 1N aqueous sodium hydroxide solution
  6. extractionextracted with two 300-ml portions of ethyl acetate
  7. washwashed with water
  8. dry with materiala saturated aqueous sodium chloride solution in this order, and dried with anhydrous magnesium sulfate
  9. customThe solvent was removed by distillation under reduced pressure
  10. customThe resulting crystal was recrystallized from methanol

Sources & evidence

ORD record
ord-ca698564beea412ca46983ba653e4e89
Source dataset
uspto-grants-1990_09
Patent number
US04954518

Reaction notes

Loading…