Sodium Chloride → HCID 12795081, compound

HRID 648004Notes

Reaction equation

HRID 648004 reaction equation
[H-].[Na+].CCCCCC.CS(O[CH2:14][CH2:15][CH2:16][CH2:17][N:18]1[CH:22]=[CH:21][CH:20]=[C:19]1[CH2:23][C:24]#[N:25])(=O)=O.[Cl-].[Na+]>CN(C)C=O>[C:24]([CH:23]1[CH2:14][CH2:15][CH2:16][CH2:17][N:18]2[CH:22]=[CH:21][CH:20]=[C:19]12)#[N:25]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 8058HexaneHCID 24758Sodium hydride2×HCID 12795073HCID 12795073, compound

Product 1

HCID 12795081HCID 12795081, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a stirred suspension of sodium hydride (obtained from 2.5 g. of 50% sodium hydride in mineral oil which had been freed of the carrier with hexane) in anhydrous dimethylformamide (60 ml.), maintained in an atmosphere of nitrogen and cooled to -5°, is added a solution of 1-(4-methansulfonyloxybutyl)pyrrol-2-acetonitrile (10 g, 0.062 moles) in dimethylformamide (40 ml.) at a rate such that the temperature is maintained at 10°-15° C. After the addition, stirring at this temperature is continued for 1 hours, and then a dilute sodium chloride solution (500 ml.) is added. The product is extracted into benzene (4×200 ml.), the extract is washed with water (4×500 ml.), dried, and evaporated in vacuo. The residue is purified by column chromatography on silica gel using hexane-ethyl acetate (95:5) as the eluting solvent to give a crude product in a 69% yield. Crystallization from acetone-hexane gives 9-cyano-6,7,8,9-tetrahydro-5H-pyrrolo[1,2-a]azepine (Formula (XIX) where n is 1), m.p. of 70°-72° C.

Workup

  1. customobtained from 2.5 g
  2. temperaturemaintained in an atmosphere of nitrogen
  3. temperaturecooled to -5°
  4. temperatureis maintained at 10°-15° C
  5. additionAfter the addition
  6. extractionThe product is extracted into benzene (4×200 ml.)
  7. washthe extract is washed with water (4×500 ml.)
  8. customdried
  9. customevaporated in vacuo
  10. customThe residue is purified by column chromatography on silica gel
  11. customto give a crude product in a 69% yield
  12. customCrystallization from acetone-hexane

Sources & evidence

ORD record
ord-65a7fe258118463b94fe2b20bf6e85a3
Source dataset
uspto-grants-1983_10
Patent number
US04410534

Reaction notes

Loading…