Thionyl Chloride → HCID 19754781, compound

HRID 1588857Notes

Reaction equation

HRID 1588857 reaction equation
[NH:1]([CH2:8][C:9]([O:11][CH:12]1[CH2:14][CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:15][C:16]1[CH:17]=[C:18]([NH:22][C:23](=[O:29])[NH:24][CH2:25][C:26](O)=[O:27])[CH:19]=[CH:20][CH:21]=1.S(Cl)(Cl)=O.[C:34](=O)([O-])O.[Na+]>ClCCCl.C(Cl)Cl>[CH3:15][C:16]1[CH:17]=[C:18]([NH:22][C:23](=[O:29])[NH:24][CH2:25][C:26]([N:1]([CH2:8][C:9]([O:11][CH2:12][CH:14]2[CH2:13][CH2:34]2)=[O:10])[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:27])[CH:19]=[CH:20][CH:21]=1

Participants

7

Reactant 4

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 149969602-{[(3-Methylphenyl)carbamoyl]amino}acetic acidHCID 19754785HCID 19754785, compound

Product 1

HCID 19754781HCID 19754781, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

A suspension of cyclopropyl 2-anilinoacetate (2.9 g) and 2-[3-(3-methylphenyl)ureido]acetic acid in anhydrous 1,2-dichloroethane (50 cc) is heated to reflux. Thionyl chloride (1.0 cc) is then added, refluxing being maintained until the gaseous evolution has ceased. The reaction mixture is then poured into saturated aqueous sodium hydrogen carbonate solution (30 cc) and thereafter methylene chloride (50 cc) is added. The organic phase is washed with distilled water (50 cc), dried over magnesium sulphate and concentrated to dryness under reduced pressure (2.7 kPa) at 40° C. After recrystallization in acetonitrile, cyclopropylmethyl 2-{2-[3-(3-methylphenyl)ureido]-N-phenylacetamido}acetate (1.6 g), m.p. 158° C., is obtained.

Workup

  1. temperatureis heated to reflux
  2. temperaturerefluxing
  3. temperaturebeing maintained until the gaseous evolution
  4. washThe organic phase is washed with distilled water (50 cc)
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated to dryness under reduced pressure (2.7 kPa) at 40° C
  7. customAfter recrystallization in acetonitrile

Sources & evidence

ORD record
ord-421958c93d2e4554914e0b4358d2d8bf
Source dataset
uspto-grants-1993_06
Patent number
US05223529

Reaction notes

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