Acetonitrile → HCID 20391512, compound

HRID 1863451Notes

Reaction equation

HRID 1863451 reaction equation
C(=O)([O-])[O-:2].[Ca+2].C(#N)C.[CH3:9][N:10]([CH3:32])[CH2:11][CH2:12][C:13]1([C:19]2[N:20]([CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[F:31])[CH:21]=[CH:22][CH:23]=2)SCCCS1>CCCCCC>[CH3:9][N:10]([CH3:32])[CH2:11][CH2:12][C:13]([C:19]1[N:20]([CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[F:31])[CH:21]=[CH:22][CH:23]=1)=[O:2]

Participants

5

Reactant 3

HCID 6342Acetonitrile2×HCID 10112Calcium CarbonateHCID 57489120HCID 57489120, compound

Product 1

HCID 20391512HCID 20391512, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

To a solution of 28.1 g of mercuric chloride and 10.3 g of calcium carbonate in 150 ml of aqueous 80% acetonitrile is added under nitrogen a solution of 17.0 g of 2-(2-dimethylaminoethyl)-2-[1-(o-fluorobenzyl)-2-pyrryl]-1,3-dithiane in 100 ml of aqueous 80% acetonitrile. The reaction mixture is stirred at reflux for 4 hours, the mixture is permitted to cool and filtered through celite. The filter cake is washed with a hexane-dichloromethane mixture and the washed solution is washed successively with a 5 M aqueous ammonium acetate solution and water, dried and filtered. The solvents are evaporated off leaving a dark oil which solidifies upon trituration with n-hexane to give the solid product of 2-(3-dimethylaminopropionyl)-1-(o-fluorobenzyl)pyrrole.

Workup

  1. temperatureat reflux for 4 hours
  2. temperatureto cool
  3. filtrationfiltered through celite
  4. washThe filter cake is washed with a hexane-dichloromethane mixture
  5. washthe washed solution is washed successively with a 5 M aqueous ammonium acetate solution and water
  6. customdried
  7. filtrationfiltered
  8. customThe solvents are evaporated off
  9. customleaving a dark oil which

Sources & evidence

ORD record
ord-85032068a0694ac6b64a7980328c857d
Source dataset
uspto-grants-1979_09
Patent number
US04169095

Reaction notes

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