Methyl chloroacetate → HCID 19829858, compound

HRID 1493608Notes

Reaction equation

HRID 1493608 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].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:5][C:4]1[CH:6]=[CH:7][CH:8]=[C:2]([I:1])[CH:3]=1

Participants

6

Reactant 4

HCID 7295Methyl chloroacetateHCID 8857Ethyl AcetateHCID 122713-IodoanilineHCID 516892Sodium Bicarbonate

Product 1

HCID 19829858HCID 19829858, compoundYield 150.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 3-iodoaniline (40.0 g), methyl chloroacetate (37.12 g) and sodium bicarbonate (30.75 g) was heated in acetonitrile (400 ml) at reflux for 2 days under nitrogen. Ethyl acetate (250 ml) was then added and the mixture was washed with water (2×250 ml) dried and evaporated to give an oil (ca. 80 g), a sample of which (1.2 g) was purified by FCC eluting with ether-petroleum ether (7-3) to give the title compound (Intermediate 27; 0.8 g) as a solid, m.p. 83°.

Workup

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

Sources & evidence

ORD record
ord-885659d1d55744a4940bc229ab104344
Source dataset
uspto-grants-1991_06
Patent number
US05023255

Reaction notes

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