Methyl chloroacetate → HCID 11571893, compound

HRID 1493598Notes

Reaction equation

HRID 1493598 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[CH:3]=1.Cl[CH2:10][C:11]([O:13][CH3:14])=[O:12].C(=O)(O)[O-].[Na+].C(OCC)(=O)C>C(#N)C>[CH3:14][O:13][C:11](=[O:12])[CH2:10][NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[CH:3]=1

Participants

6

Reactant 4

HCID 7295Methyl chloroacetateHCID 7934m-ToluidineHCID 8857Ethyl AcetateHCID 516892Sodium Bicarbonate

Product 1

HCID 11571893HCID 11571893, compoundYield 130.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of m-toluidine (55.0 g), methyl chloroacetate (85.0 g) and sodium bicarbonate (86.2 g) in acetonitrile (400 ml) was heated at reflux for 2 days under nitrogen. Ethyl acetate (250 ml) was added and the mixture was washed with water (2×250 ml), dried and evaporated to give an oil (120 g), a sample of which (1.4 g) was purified by FCC eluting with System A (3:7) to give the title compound (0.8 g) as a solid, m.p. 40°.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 days under nitrogen
  3. washthe mixture was washed with water (2×250 ml)
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-03258b4a24fe423a9a1bb904e62f0700
Source dataset
uspto-grants-1991_06
Patent number
US05023255

Reaction notes

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