Triethylamine → HCID 69432265, compound

HRID 970762Notes

Reaction equation

HRID 970762 reaction equation
C(N(CC)CC)C.Cl.[C:9]([NH:17][CH2:18][CH:19]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[NH2:20])(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.Cl[C:28]([O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:29]>ClCCl>[CH2:31]([O:30][C:28]([NH:20][CH:19]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:18][NH:17][C:9](=[O:16])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)=[O:29])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 69429904HCID 69429904, compound

Product 1

HCID 69432265HCID 69432265, compoundYield 82.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
5 °C

Procedure

0.12 g of triethylamine was added to 10 ml of a solution of 0.25 g of N-benzoyl-2-phenyl-1,2-ethylenediamine hydrochloride and 0.17 g of benzyl chloroformate in dichloromethane under ice cooling, and the mixture was stirred at 5° C. for 30 minutes and at room temperature for 3 hours. The reaction mixture was rinsed with water, the organic layer was dried over magnesium sulfate anhydrous, and the residual oily material obtained under a reduced pressure was purified by column chromatography on silica gel (2:1 hexane/ethyl acetate) to obtain 0.28 g of the title compound as colorless crystals.

Workup

  1. washThe reaction mixture was rinsed with water
  2. dry with materialthe organic layer was dried over magnesium sulfate anhydrous
  3. customthe residual oily material obtained under a reduced pressure
  4. customwas purified by column chromatography on silica gel (2:1 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-86f88af449d94636a7560fa24deabacb
Source dataset
uspto-grants-2007_12
Patent number
US07312245B2

Reaction notes

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