Pyridine → HCID 20229455, compound

HRID 2291165Notes

Reaction equation

HRID 2291165 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[C:12](=[O:16])[CH2:13][CH2:14][Cl:15])[NH:8][C:7](=[O:17])[CH2:6][CH2:5]2.N1C=CC=CC=1.[CH3:24][S:25](Cl)(=[O:27])=[O:26].[Cl-].[Na+]>CN(C)C=O>[CH3:24][S:25]([O:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[C:12](=[O:16])[CH2:13][CH2:14][Cl:15])[NH:8][C:7](=[O:17])[CH2:6][CH2:5]2)(=[O:27])=[O:26]

Participants

6

Reactant 4

HCID 1049PyridineHCID 5234Sodium ChlorideHCID 31297Methanesulfonyl chlorideHCID 13120785HCID 13120785, compound

Product 1

HCID 20229455HCID 20229455, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5.06 Grams of 6-hydroxy-7-(3-chloropropionyl)-3,4-dihydrocarbostyril and 1.8 g of anhydrous pyridine were mixed with 50 ml of dimethylformamide. Then the mixture was cooled with ice and 2.5 g of methanesulfonyl chloride was added to the mixture and stirred at a room temperature for 3 hours. The reaction mixture was poured into 100 ml of a saturated sodium chloride solution and extracted with chloroform. The chloroform layer was washed with water, dried and chloroform was removed by distillation under a reduced pressure to obtain a residue. The residue was crystallized by adding 80 ml of hexane to obtain crude crystals. The crude materials were collected by filtration and were recrystallized from ethanol to obtain 4.5 g of 6-methylsulfonyloxy-7-(3-chloropropionyl)-3,4-dihydrocarbostyril in white crystals.

Workup

  1. additionwas added to the mixture
  2. extractionextracted with chloroform
  3. washThe chloroform layer was washed with water
  4. customdried
  5. customchloroform was removed by distillation under a reduced pressure
  6. customto obtain a residue
  7. customThe residue was crystallized
  8. additionby adding 80 ml of hexane
  9. customto obtain crude crystals
  10. filtrationThe crude materials were collected by filtration
  11. customwere recrystallized from ethanol

Sources & evidence

ORD record
ord-22e1a5e24b12435b84c2157869798e70
Source dataset
uspto-grants-1986_10
Patent number
US04619932

Reaction notes

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