Dimethylformamide → HCID 69744622, compound

HRID 1760060Notes

Reaction equation

HRID 1760060 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]#[N:16])=[CH:11][C:10]=1[CH2:17][C:18]([OH:20])=[O:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:21]N(C)C=O.S(Cl)(Cl)=O>ClCCl>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]#[N:16])=[CH:11][C:10]=1[CH2:17][C:18]([O:20][CH3:21])=[O:19])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 11230933HCID 11230933, compound

Product 1

HCID 69744622HCID 69744622, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

10.0 g (0.037 mol) of (2-benzyloxy-5-cyano-phenyl)-acetic acid are refluxed for two hours in 65 ml dichloromethane, 0.1 ml of dimethylformamide and 8.1 ml (0.11 mol) of thionyl chloride. Then the mixture is concentrated by evaporation, the residue is combined with 55 ml of methanol and refluxed for one hour. After cooling the mixture is suction filtered, washed with ether/petroleum ether and dried at 50° C.

Workup

  1. concentrationThen the mixture is concentrated by evaporation
  2. temperaturerefluxed for one hour
  3. temperatureAfter cooling the mixture
  4. filtrationfiltered
  5. washwashed with ether/petroleum ether
  6. customdried at 50° C.

Sources & evidence

ORD record
ord-618e36794d8a4dff9a73f4d87cdd42f4
Source dataset
uspto-grants-2005_01
Patent number
US06838565B2

Reaction notes

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