Benzenesulfonyl chloride → HCID 20450620, compound

HRID 1463017Notes

Reaction equation

HRID 1463017 reaction equation
C1(S(Cl)(=O)=O)C=CC=CC=1.[CH2:11]([CH:16]1[O:21][C:20]2[CH:22]=[CH:23][C:24]([C:26]([NH2:28])=O)=[CH:25][C:19]=2[CH2:18][O:17]1)[CH2:12][CH2:13][CH2:14][CH3:15]>N1C=CC=CC=1>[CH2:11]([CH:16]1[O:21][C:20]2[CH:22]=[CH:23][C:24]([C:26]#[N:28])=[CH:25][C:19]=2[CH2:18][O:17]1)[CH2:12][CH2:13][CH2:14][CH3:15]

Participants

4

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 20450711HCID 20450711, compound

Product 1

HCID 20450620HCID 20450620, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1.85 ml of benzenesulphonyl chloride are added dropwise while stirring to a suspension of 1.2 g of 2-pentyl-1,3-benzodioxan-6-carboxamide in 10 ml of pyridine. The mixture is left to stand overnight and then the solution is extracted with 15 ml of 1N sodium hydroxide and ether. The aqueous phase is separated and back-extracted with ether. The combined organic phase is washed with 1N sodium hydroxide and then with water, dried over sodium sulphate, filtered and concentrated. The residue is treated with hot hexane. The mixture is decanted off from insoluble material and the solution is evaporated. The crude product is recrystallized once from hexane and twice from isopropanol. There is obtained 2-pentyl-1,3-benzodioxan-6-carbonitrile; m.p. 40.5°-41° C. (not liquid crystalline).

Workup

  1. waitThe mixture is left
  2. extractionthe solution is extracted with 15 ml of 1N sodium hydroxide and ether
  3. customThe aqueous phase is separated
  4. extractionback-extracted with ether
  5. washThe combined organic phase is washed with 1N sodium hydroxide
  6. dry with materialwith water, dried over sodium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. additionThe residue is treated with hot hexane
  10. customThe mixture is decanted off from insoluble material
  11. customthe solution is evaporated
  12. customThe crude product is recrystallized once from hexane and twice from isopropanol

Sources & evidence

ORD record
ord-4a2eb46994314a2bbf207d3af74f97e8
Source dataset
uspto-grants-1984_07
Patent number
US04462923

Reaction notes

Loading…