Methyl chloroacetate → HCID 22120793, compound

HRID 1493619Notes

Reaction equation

HRID 1493619 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([CH:12]=[CH:13][CH:14]=1)[NH2:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)(O)[O-].[Na+].Cl[CH2:21][C:22]([O:24][CH3:25])=[O:23]>O>[CH3:25][O:24][C:22](=[O:23])[CH2:21][NH:11][C:10]1[CH:12]=[CH:13][CH:14]=[C:8]([O:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:9]=1

Participants

5

Reactant 3

HCID 7295Methyl chloroacetateHCID 771353-PhenoxyanilineHCID 516892Sodium Bicarbonate

Product 1

HCID 22120793HCID 22120793, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3-phenoxyaniline (25 g, 0.135 mol), sodium bicarbonate (22.7 g, 0.27 mol) and methyl chloroacetate (15.5 ml, 0.2025 mol) was heated at 90°-100° C. with vigorous stirring for 20 h. The mixture was allowed to cool to room temperature and was then poured into water (200 ml) and extracted with dichloromethane (2×100 ml). The organic extract was washed with 2N hydrochloric acid (2×100 ml), water (2×100 ml) and then dried and evaporated to give a grey/green solid. This was triturated with hexane (400 ml) and filtered to give the title compound as a grey/green solid (18.4 g, 53%), m.p 44°-45°.

Workup

  1. temperaturewas heated at 90°-100° C.
  2. extractionextracted with dichloromethane (2×100 ml)
  3. extractionThe organic extract
  4. washwas washed with 2N hydrochloric acid (2×100 ml), water (2×100 ml)
  5. customdried
  6. customevaporated
  7. customto give a grey/green solid
  8. customThis was triturated with hexane (400 ml)
  9. filtrationfiltered

Sources & evidence

ORD record
ord-b85fcdfbae374b30b1ec75bfc3613606
Source dataset
uspto-grants-1991_06
Patent number
US05023255

Reaction notes

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