Methyl chloroacetate → HCID 20074977, compound

HRID 703810Notes

Reaction equation

HRID 703810 reaction equation
C(=O)(O)[O-].[Na+].Cl[CH2:7][C:8]([O:10][CH3:11])=[O:9].[NH2:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[C:16]#[N:17]>CCOCC>[CH3:11][O:10][C:8](=[O:9])[CH2:7][NH:12][C:13]1[CH:20]=[CH:19][CH:18]=[C:15]([C:16]#[N:17])[CH:14]=1

Participants

5

Reactant 3

HCID 7295Methyl chloroacetateHCID 167023-AminobenzonitrileHCID 516892Sodium Bicarbonate

Product 1

HCID 20074977HCID 20074977, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of sodium bicarbonate (35.5 g), methyl chloroacetate (28 ml) and 3-aminobenzonitrile (25 g) 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 solid precipitate was filtered off and the filtrate was retained. The solid was dissolved in dichloromethane (400 ml) and washed with water (200 ml) followed by dilute hydrochloric acid (200 ml). The organic phase was dried and concentrated in vacuo to give the title compound as a solid (13.8 g), m.p. 91.5°-92.5°. The previously obtained filtrate was washed with water (100 ml), dilute hydrochloric acid (200 ml) and water (100 ml), then dried and concentrated in vacuo. The resultant solid was triturated with ether to give a further batch of the title compound (11.7 g).

Workup

  1. temperatureHeating at 90°
  2. waitwas continued overnight
  3. temperaturethe mixture was then cooled
  4. filtrationThe solid precipitate was filtered off
  5. dissolutionThe solid was dissolved in dichloromethane (400 ml)
  6. washwashed with water (200 ml)
  7. customThe organic phase was dried
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-97d8c2c95ab0417791b2669d809120aa
Source dataset
uspto-grants-1991_01
Patent number
US04985427

Reaction notes

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