Benzoyl chloride → HCID 69426299, compound

HRID 970760Notes

Reaction equation

HRID 970760 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:10][O:11][C:12]([NH:14][CH:15]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:16][NH2:17])=[O:13].C(N(CC)CC)C>ClCCl>[CH3:10][O:11][C:12]([NH:14][CH:15]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:16][NH:17][C:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:13]

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 22935185HCID 22935185, compound

Product 1

HCID 69426299HCID 69426299, compoundYield 72.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
5 °C

Procedure

0.22 g of benzoyl chloride was added to 10 ml of a solution of 0.25 g of N-(methoxycarbonyl)-1-phenylethylenediamine and 0.2 g of triethylamine in dichloromethane under ice cooling, and the mixture was stirred for 30 minutes at 5° C. 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-b9e5c63c74394a6dadb821a857eb3339
Source dataset
uspto-grants-2007_12
Patent number
US07312245B2

Reaction notes

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