Phosgene → 3-(2,3-Dichlorophenoxy)-1-pyrrolidinecarbonyl Chloride

HRID 464423Notes

Reaction equation

HRID 464423 reaction equation
[C:1]([Cl:4])(Cl)=[O:2].C([N:12]1[CH2:16][CH2:15][CH:14]([O:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[C:19]=2[Cl:25])[CH2:13]1)C1C=CC=CC=1.C(Cl)C1C=CC=CC=1>C1C=CC=CC=1>[Cl:25][C:19]1[C:20]([Cl:24])=[CH:21][CH:22]=[CH:23][C:18]=1[O:17][CH:14]1[CH2:15][CH2:16][N:12]([C:1]([Cl:4])=[O:2])[CH2:13]1

Participants

5

Reactant 3

HCID 6371PhosgeneHCID 7503Benzyl ChlorideHCID 20263046HCID 20263046, compound

Product 1

HCID 202630113-(2,3-Dichlorophenoxy)-1-pyrrolidinecarbonyl Chloride

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To a solution of 200 ml of 2M phosgene in benzene, stirred under nitrogen gas, was added 96 g (0.3 mole) of 1-benzyl-3-(2,3-dichlorophenoxy)pyrrolidine in 300 ml of benzene. The reaction mixture was allowed to stir overnight and then concentrated to an oil. The oil was triturated with 30/60 petroleum ether to give an oil. Solid product, 89 g, was obtained containing a trace of benzyl chloride. The yield was nearly quantitative.

Workup

  1. concentrationconcentrated to an oil
  2. customThe oil was triturated with 30/60 petroleum ether
  3. customto give an oil
  4. customSolid product, 89 g, was obtained

Sources & evidence

ORD record
ord-da8f9403694945d6bb9ea18426e97203
Source dataset
uspto-grants-1985_10
Patent number
US04547514

Reaction notes

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