Dimethylformamide → N-(4'-Chlorobiphenyl-4-carbonyl)-2(R)-phenyl-aziridine

HRID 54518Notes

Reaction equation

HRID 54518 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([OH:16])=O)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[C:17]1(N2CC2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[CH3:26][N:27]([CH:29]=O)C>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[CH:10][C:11]([C:14]([N:27]3[CH2:29][C@H:26]3[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)=[O:16])=[CH:12][CH:13]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 6228Dimethylformamide2×HCID 696731-PhenylaziridineHCID 6160024-Biphenylcarboxylic acid, 4'-chloro-

Product 1

HCID 22872208N-(4'-Chlorobiphenyl-4-carbonyl)-2(R)-phenyl-aziridine

Procedure

To a solution of 0.232 g of 4'-chlorobiphenyl-4-carboxylic acid in 3 ml of dry DMF, 0.18 g of N,N'-carbonyl-diimidazole are added with stirring at room temperature under argon atmosphere. After one hour a solution of 0.12 g of phenyl-aziridine in 0.5 ml of dry DMF is added dropwise. The reaction mixture is stirred for 21 hours and thereafter worked up as described in example 1. The compound is obtained as a pale yellow oil and used without purification in the next step.

Workup

  1. stirringThe reaction mixture is stirred for 21 hours
  2. customThe compound is obtained as a pale yellow oil
  3. customused without purification in the next step

Sources & evidence

ORD record
ord-50be94b7d1fa41d4856b0969252a7d2c
Source dataset
uspto-grants-1997_04
Patent number
US05622982

Reaction notes

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