Thionyl Chloride → HCID 53683189, compound

HRID 619276Notes

Reaction equation

HRID 619276 reaction equation
S(Cl)([Cl:3])=O.[N:5]([C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][C:16]=1[C@H:17]([NH:19][C:20]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21])[CH3:18])[C:11](O)=[O:12])=[N+:6]=[N-:7]>CN(C)C=O.ClCCl>[N:5]([C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][C:16]=1[C@H:17]([NH:19][C:20]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21])[CH3:18])[C:11]([Cl:3])=[O:12])=[N+:6]=[N-:7]

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 53885999HCID 53885999, compound

Product 1

HCID 53683189HCID 53683189, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

Thionyl chloride (4 ml) and dimethylformamide (1 drop) were added to a solution of (R)-3-azido-4-(1-benzyloxycarbonylaminoethyl)benzoic acid in dichloromethane (20 ml), and the mixture was refluxed under heating for 2 hours. After the reaction, the solvent was evaporated under reduced pressure. The obtained residue was boiled with benzene to give 1.65 g of (R)-3-azido-4-(1-benzyloxycarbonylaminoethyl)benzoyl chloride as yellow crystals.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 2 hours
  3. customAfter the reaction
  4. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-cb917f4110aa4e76878bfab917949a21
Source dataset
uspto-grants-1999_09
Patent number
US05958944

Reaction notes

Loading…