Acetonitrile → HCID 16114316, compound

HRID 1374935Notes

Reaction equation

HRID 1374935 reaction equation
[Cl:1][CH2:2][C:3]([N:5]1[CH2:9][CH2:8][CH2:7][CH2:6]1)=[O:4].[CH3:10][N:11]1[CH:15]=[CH:14][N:13]=[C:12]1[CH3:16].C(#N)C>C(OC)(C)(C)C>[Cl-:1].[N:5]1([C:3](=[O:4])[CH2:2][N:13]2[CH:14]=[CH:15][N+:11]([CH3:10])=[C:12]2[CH3:16])[CH2:9][CH2:8][CH2:7][CH2:6]1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 156171,2-DimethylimidazoleHCID 884401-(Chloroacetyl)pyrrolidine

Product 1

HCID 16114316HCID 16114316, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of N-(chloroacetyl)pyrrolidine (2.0 g, 13.55 mmol) and 1,2-dimethylimidazole (1.3 g, 13.5 mmol) were heated neat at 110° C. for 3 hours. To the reaction mixture was added acetonitrile (5 mL), and heating was continued for 20 minutes. Tert-butyl methylether (10 mL) was added, and the resulting mixture was allowed to stand at room temperature overnight. The product was recovered by filtration, and washed with a mixture of tert-butyl methyl ether and acetonitrile (7:3 v/v, 50 mL). The crude product was recrystallized from a mixture of acetonitrile and tert-butyl methyl ether to obtain 1.23 g (41%) of a white solid; mp 191–193° C.

Workup

  1. temperatureheating
  2. waitto stand at room temperature overnight
  3. filtrationThe product was recovered by filtration
  4. washwashed with a mixture of tert-butyl methyl ether and acetonitrile (7:3 v/v, 50 mL)
  5. customThe crude product was recrystallized from a mixture of acetonitrile and tert-butyl methyl ether

Sources & evidence

ORD record
ord-c3aeca193e994a63bdcf8639e98baea9
Source dataset
uspto-grants-2007_01
Patent number
US07166625B2

Reaction notes

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