1,2-Dichlorobenzene → HCID 54738298, compound

HRID 2165263Notes

Reaction equation

HRID 2165263 reaction equation
[NH2:1][C:2]([CH2:8][CH3:9])=[CH:3][C:4](OC)=[O:5].[C:10]([O:18]CC)(=O)[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13].C[O-].[Na+].ClC1C=CC=CC=1Cl>CO.C(O)C>[C:12]([C:11]1[C:10](=[O:18])[NH:1][C:2]([CH2:8][CH3:9])=[CH:3][C:4]=1[OH:5])([O:14][CH2:15][CH3:16])=[O:13]

Participants

7

Reactant 4

HCID 72391,2-DichlorobenzeneHCID 7761Diethyl MalonateHCID 10942334Sodium MethoxideHCID 57860398Methyl 3-aminopent-2-enoate

Product 1

HCID 54738298HCID 54738298, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 887MethanolSolvent2×

Conditions

Temperature
160 °C

Procedure

113.6 g (0.88 mol) of methyl 3-amino-2-pentenoate and 128 g (0.8 mol) of diethyl malonate are added to a solution of 259.2 g (0.8 mol) of 21% strength sodium methoxide solution in methanol and 130 g of ethanol. After addition of 800 ml of 1,2-dichlorobenzene, a mixture of methanol and ethanol is removed by distillation in the course of one hour and the remaining suspension is heated to 160° C. for two hours. After cooling, 600 ml of water are added, and the organic phase is separated off, extracted using water and then discarded. The combined aqueous phases are washed with ether, and the aqueous phase is separated off, acidified using hydrochloric acid and filtered off with suction.

Workup

  1. customis removed by distillation in the course of one hour
  2. temperatureAfter cooling
  3. addition600 ml of water are added
  4. customthe organic phase is separated off
  5. extractionextracted
  6. washThe combined aqueous phases are washed with ether
  7. customthe aqueous phase is separated off
  8. filtrationfiltered off with suction

Sources & evidence

ORD record
ord-b070b1b276264084921081460771fe05
Source dataset
uspto-grants-1990_07
Patent number
US04939262

Reaction notes

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