Thionyl Chloride → HCID 21505318, compound

HRID 1287573Notes

Reaction equation

HRID 1287573 reaction equation
[CH2:1]([N:8]1[CH2:15][CH2:14][CH2:13][C@H:9]1[C:10]([OH:12])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[CH3:20][NH:21][C:22]1[C:23](=[CH:29][CH:30]=[CH:31][CH:32]=1)[C:24]([O:26][CH2:27][CH3:28])=[O:25]>C1C=CC=CC=1>[CH2:1]([N:8]1[CH2:15][CH2:14][CH2:13][CH:9]1[C:10]([N:21]([CH3:20])[C:22]1[C:23](=[CH:29][CH:30]=[CH:31][CH:32]=1)[C:24]([O:26][CH2:27][CH3:28])=[O:25])=[O:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 101365Ethyl N-methylanthranilateHCID 728719N-Benzyl-L-proline

Product 1

HCID 21505318HCID 21505318, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 21 g. of N-benzylproline and 300 ml. of benzene is stirred and 12 g. of thionyl chloride is added dropwise. The reaction mixture is heated on the steam bath for 2 hours, and 18 g. of ethyl N-methylanthranilate are added. The mixture is heated at reflux temperature for 6 hours, washed with dilute sodium hydroxide and concentrated. The residue is purified by partition chromatography and ethyl N-(N-benzyl-2-pyrrolidinylcarbonyl)-N-methylanthranilate is obtained.

Workup

  1. additionA mixture of 21 g
  2. temperatureThe reaction mixture is heated on the steam bath for 2 hours
  3. temperatureThe mixture is heated
  4. temperatureat reflux temperature for 6 hours
  5. washwashed with dilute sodium hydroxide
  6. concentrationconcentrated
  7. customThe residue is purified
  8. customby partition chromatography

Sources & evidence

ORD record
ord-848e416cf47a49e08e9fda710d11c90b
Source dataset
uspto-grants-1976_10
Patent number
US03985732

Reaction notes

Loading…