Methyl chloroacetate → HCID 3615705, compound

HRID 1493633Notes

Reaction equation

HRID 1493633 reaction equation
[O:1]([C:8]1[CH:14]=[CH:13][C:11]([NH2:12])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[CH2:16][C:17]([O:19][CH3:20])=[O:18].C(=O)(O)[O-].[Na+]>CCCCCC>[O:1]([C:8]1[CH:9]=[CH:10][C:11]([NH:12][CH2:16][C:17]([O:19][CH3:20])=[O:18])=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7295Methyl chloroacetateHCID 8764(4-Aminophenoxy)benzeneHCID 516892Sodium Bicarbonate

Product 1

HCID 3615705HCID 3615705, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A mixture of 4-phenoxyaniline (30 g, 0.162 mol), methyl chloroacetate (21.3 ml, 0.243 mol) and sodium bicarbonate (27.2 g, 0.324 mol) was heated at 100°-120° C. with magnetic stirring for 24 hours. The resulting semi-solid was partitioned between dichloromethane (300 ml) and water (300 ml) then separated. The aqueous layer was extracted with dichloromethane (200 ml) and the organic extracts were combined. The extracts were washed with 2N hydrochloric acid (2×200 ml) and water (2×200 ml), dried (MgSO4) and evaporated to give a brown oil. This was heated with hexane (300 ml) to give an oil suspension. The hexane was decanted off and residual oil crystallised on cooling. The solid was triturated with ether/hexane 1:1 and filtered to give a brown solid (13.6 g, 33%) m.p. 80°-82° C. A second crop of a pale yellow solid was also given (10.5 g, 25%).

Workup

  1. temperaturewas heated at 100°-120° C.
  2. customThe resulting semi-solid was partitioned between dichloromethane (300 ml) and water (300 ml)
  3. customthen separated
  4. extractionThe aqueous layer was extracted with dichloromethane (200 ml)
  5. washThe extracts were washed with 2N hydrochloric acid (2×200 ml) and water (2×200 ml)
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customto give a brown oil
  9. customto give an oil suspension
  10. customThe hexane was decanted off
  11. customresidual oil crystallised
  12. temperatureon cooling
  13. customThe solid was triturated with ether/hexane 1:1
  14. filtrationfiltered

Sources & evidence

ORD record
ord-779b916c960a4cbfbb20504314385c02
Source dataset
uspto-grants-1991_06
Patent number
US05023255

Reaction notes

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