Ethyl 4-chlorobenzoate → 1,1-Dimethylethyl N-[2-[(4-chlorobenzoyl)amino]ethyl]carbamate

HRID 2255101Notes

Reaction equation

HRID 2255101 reaction equation
[Cl:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8]CC)=O)=[CH:4][CH:3]=1.[C:13]([O:17][C:18]([NH:20][CH2:21][CH2:22][NH2:23])=[O:19])([CH3:16])([CH3:15])[CH3:14]>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([NH:23][CH2:22][CH2:21][NH:20][C:18](=[O:19])[O:17][C:13]([CH3:15])([CH3:14])[CH3:16])=[O:8])=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 81785Ethyl 4-chlorobenzoateHCID 187201N-BOC-ethylenediamine

Product 1

HCID 135768931,1-Dimethylethyl N-[2-[(4-chlorobenzoyl)amino]ethyl]carbamateYield 26.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

9.25 g of ethyl 4-chlorobenzoate and 16.0 g of N-(t-butoxycarbonyl)ethylenediamine are stirred at 130° for 15 hours. The mixture is cooled to room temperature, taken up in 100 ml of water and extracted three times with 50 ml of ethyl acetate each time. The ethyl acetate extract is washed twice with 50 ml of water each time, dried over sodium sulfate and evaporated to dryness. The crystalline residue is taken up in isopropyl ether and filtered off under suction. There are obtained 3.9 g of t-butyl [2-(4-chlorobenzamido)ethyl]carbamate, m.p. 141°-143°.

Workup

  1. extractionextracted three times with 50 ml of ethyl acetate each time
  2. extractionThe ethyl acetate extract
  3. washis washed twice with 50 ml of water each time
  4. dry with materialdried over sodium sulfate
  5. customevaporated to dryness
  6. filtrationfiltered off under suction

Sources & evidence

ORD record
ord-93f7399e32ea45c39194eea2b0df943c
Source dataset
uspto-grants-1993_08
Patent number
US05238962

Reaction notes

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