Water → 5-Hydroxy-8-methanesulfonylamino-3,4-dihydrocarbostyril

HRID 26031Notes

Reaction equation

HRID 26031 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([OH:13])=[C:6]2[C:11]=1[NH:10][C:9](=[O:12])[CH2:8][CH2:7]2.C([O-])(=O)C.[Na+].[CH3:19][S:20](Cl)(=[O:22])=[O:21].O>C(O)(=O)C>[OH:13][C:5]1[CH:4]=[CH:3][C:2]([NH:1][S:20]([CH3:19])(=[O:22])=[O:21])=[C:11]2[C:6]=1[CH2:7][CH2:8][C:9](=[O:12])[NH:10]2

Participants

6

Reactant 4

HCID 962WaterHCID 31297Methanesulfonyl chlorideHCID 517045Sodium AcetateHCID 213263108-Amino-5-hydroxy-3,4-dihydrocarbostyril

Product 1

HCID 213263125-Hydroxy-8-methanesulfonylamino-3,4-dihydrocarbostyrilYield 54.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

5.0 g of 8-amino-5-hydroxy-3,4-dihydrocarbostyril was suspended in 30 ml of acetic acid, and 4.0 g of sodium acetate was added to the suspension while stirring. 3.5 g of methanesulfonyl chloride was then added to the mixture followed by heating for 7 hours while refluxing. After completion of the reaction, 100 ml of water was added to the reaction mixture which was then concentrated to dryness under reduced pressure. The resulting residue was added to 200 ml of water, and the mixture was stirred. The crystals formed were recovered by filtration, washed with water and recrystallized from methanol to obtain 3.89 g of 5-hydroxy-8-methanesulfonylamino-3,4-dihydrocarbostyril as colorless amorphous crystals having a melting point of 269.4°-269.8° C.

Workup

  1. temperatureby heating for 7 hours
  2. temperaturewhile refluxing
  3. additionwas added to the reaction mixture which
  4. concentrationwas then concentrated to dryness under reduced pressure
  5. additionThe resulting residue was added to 200 ml of water
  6. stirringthe mixture was stirred
  7. customThe crystals formed
  8. filtrationwere recovered by filtration
  9. washwashed with water
  10. customrecrystallized from methanol

Sources & evidence

ORD record
ord-7486eb4c34be4725bb3842931c05e3eb
Source dataset
uspto-grants-1979_04
Patent number
US04147869

Reaction notes

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