Methyl chloroacetate → HCID 11629788, compound

HRID 703809Notes

Reaction equation

HRID 703809 reaction equation
C(=O)(O)[O-].[Na+].[Cl:6][C:7]1[CH:8]=[C:9]([CH:11]=[CH:12][CH:13]=1)[NH2:10].Cl[CH2:15][C:16]([O:18][CH3:19])=[O:17]>CCOCC>[CH3:19][O:18][C:16](=[O:17])[CH2:15][NH:10][C:9]1[CH:11]=[CH:12][CH:13]=[C:7]([Cl:6])[CH:8]=1

Participants

5

Reactant 3

HCID 7295Methyl chloroacetateHCID 79323-ChloroanilineHCID 516892Sodium Bicarbonate

Product 1

HCID 11629788HCID 11629788, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of sodium bicarbonate (66 g), 3-chloroaniline (50 g) and methyl chloroacetate (51.5 ml) were stirred under nitrogen at 80°-100° for 6 h. Heating at 90° was continued overnight, and the mixture was then cooled and poured into ether (400 ml). The resultant suspension was stirred, chilled to 0°, the precipitated solid was filtered off and the filtrate was retained. The solid was dissolved in ethyl acetate (400 ml) and washed with water (2×200 ml), followed by dilute hydrochloric acid (200 ml). The organic phase was dried and concentrated in vacuo to give the title compound (16.4 g) as a solid, m.p. 75°-76°. The previously obtained filtrate was washed with dilute hydrochloric acid (200 ml), and the organic phase was separated, dried and concentrated in vacuo to give an oily solid. This was triturated with ether:hexane (1:1; 300 ml) and filtered off to give a further batch of the title compound (20 g).

Workup

  1. temperatureHeating at 90°
  2. waitwas continued overnight
  3. temperaturethe mixture was then cooled
  4. temperaturechilled to 0°
  5. filtrationthe precipitated solid was filtered off
  6. dissolutionThe solid was dissolved in ethyl acetate (400 ml)
  7. washwashed with water (2×200 ml)
  8. customThe organic phase was dried
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bab85053286144c291524e19bcde6f1c
Source dataset
uspto-grants-1991_01
Patent number
US04985427

Reaction notes

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