Methoxyacetyl chloride → Ethyl 2,4-bis(methoxyacetylamino)benzoate

HRID 1165882Notes

Reaction equation

HRID 1165882 reaction equation
[NH2:1][C:2]1[CH:12]=[C:11]([NH2:13])[CH:10]=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH3:14][O:15][CH2:16][C:17](Cl)=[O:18]>N1C=CC=CC=1>[CH3:14][O:15][CH2:16][C:17]([NH:1][C:2]1[CH:12]=[C:11]([NH:13][C:17](=[O:18])[CH2:16][O:15][CH3:14])[CH:10]=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5])=[O:18]

Participants

4

Reactant 2

HCID 96623Methoxyacetyl chlorideHCID 22096618Ethyl 2,4-diaminobenzoate

Product 1

HCID 14699287Ethyl 2,4-bis(methoxyacetylamino)benzoate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of ethyl 2,4-diaminobenzoate (3.6 g) in pyridine (80 ml) is added dropwise methoxyacetyl chloride (4.0 ml) at room temperature. The mixture is stirred at room temperature for 3 hours, and thereafter, pyridine is distilled off under reduced pressure. To the residue are added water and chloroform. The organic layer is separated and washed with water and then with aqueous saturated sodium chloride solution, and dried over anhydrous sodium sulfate. The solvent is distilled off under reduced pressure, and the resulting oily substance is dissolved in ethyl acetate-hexane, and the solution is allowed to stand at -30° C. for 6 hours. The precipitated crystals are separated by filtration to give the title compound (6.0 g) having the following physical properties.

Workup

  1. distillationpyridine is distilled off under reduced pressure
  2. additionTo the residue are added water and chloroform
  3. customThe organic layer is separated
  4. washwashed with water
  5. dry with materialwith aqueous saturated sodium chloride solution, and dried over anhydrous sodium sulfate
  6. distillationThe solvent is distilled off under reduced pressure
  7. dissolutionthe resulting oily substance is dissolved in ethyl acetate-hexane
  8. waitto stand at -30° C. for 6 hours
  9. customThe precipitated crystals are separated by filtration

Sources & evidence

ORD record
ord-c2dba8e770cd4b999a6d31eea55abdc8
Source dataset
uspto-grants-1990_03
Patent number
US04912135

Reaction notes

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