Ethyl chloroformate → HCID 12805045, compound

HRID 1649091Notes

Reaction equation

HRID 1649091 reaction equation
[NH2:1][C:2]1[CH:14]=[CH:13][C:5]([C:6]([CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[O:7])=[CH:4][CH:3]=1.Cl[C:16]([O:18][CH2:19][CH3:20])=[O:17]>O1CCCC1>[CH2:19]([O:18][C:16]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[O:7])=[CH:13][CH:14]=1)=[O:17])[CH3:20]

Participants

4

Reactant 2

HCID 10928Ethyl chloroformateHCID 2432904-(4-Aminophenyl)-4-oxobutanoic acid

Product 1

HCID 12805045HCID 12805045, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

10.0 g (51.8 millimoles) of 3-(p-aminobenzoyl)propionic acid, 6.7 g (61.7 millimoles) of ethyl chloroformate and 100 ml of absolute tetrahydrofuran are refluxed for 10 hours. The product is filtered off at 10° C., washed with water and recrystallized from dimethylformamide/water. 7.8 g (57% of theory) of 3-(p-ethoxycarbonylaminobenzoyl)-propionic acid are obtained as pale beige crystals, of melting point 206°-207° C.

Workup

  1. filtrationThe product is filtered off at 10° C.
  2. washwashed with water
  3. customrecrystallized from dimethylformamide/water

Sources & evidence

ORD record
ord-2605ef5885a3414b8319e61ed78f0d41
Source dataset
uspto-grants-1983_11
Patent number
US04415571

Reaction notes

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