4-Chlorobenzoyl chloride → 5-(4-Chlorobenzoyl)-1, 2-dihydro-1-pyrrolizinone

HRID 52195

Reaction equation

HRID 52195 reaction equation
[C:1]1(=[O:9])[C:8]2[N:4]([CH:5]=[CH:6][CH:7]=2)[CH2:3][CH2:2]1.[Cl:10][C:11]1[CH:19]=[CH:18][C:14]([C:15](Cl)=[O:16])=[CH:13][CH:12]=1>ClCC(Cl)(Cl)Cl>[Cl:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([C:5]2[N:4]3[C:8](=[CH:7][CH:6]=2)[C:1](=[O:9])[CH2:2][CH2:3]3)=[O:16])=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 85014-Chlorobenzoyl chlorideHCID 973473H-1,2-dihydro-1-pyrrolizinone

Product 1

HCID 541992345-(4-Chlorobenzoyl)-1, 2-dihydro-1-pyrrolizinoneYield 72%

Reagents, catalysts & solvents 1

HCID 124181,1,1,2-TetrachloroethaneSolvent

Procedure

To a stirred mixture of 12.1 g compound (1) and 8 g AICI3 in 40 ml tetrachloroethane was added dropwise 5.3 g 4-chlorobenzoyl chloride during 1 hour. The mixture was stirred at 40°-45° C. for 2 hours. The reaction mixture was added into 100 g ice-water. The organic layer was dried over MgSO4. Evaporated to dryness, 7 g crude product was obtained. Recrystallized from ethanol, 5.5 g of (3) was obtained as a white solid, mp 165°-166.5° C., yield 72%.

Workup

  1. dry with materialThe organic layer was dried over MgSO4
  2. customEvaporated to dryness
  3. custom7 g crude product was obtained
  4. customRecrystallized from ethanol

Sources & evidence

ORD record
ord-790094ec1bfb4f55b92d24e91ba4cfa8
Source dataset
uspto-grants-1997_04
Patent number
US05616604

Linked notes

Loading…