Toluene → HCID 13649254, compound

HRID 1200150Notes

Reaction equation

HRID 1200150 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C=CC=CC=1.[CH3:17][C:18]([NH:26][C:27](=[O:31])[CH2:28][CH2:29][NH2:30])([CH3:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(N(CC)CC)C>[CH3:25][C:18]([NH:26][C:27](=[O:31])[CH2:28][CH2:29][NH:30][C:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)([CH3:17])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 7412Benzoyl chlorideHCID 11579350HCID 11579350, compound

Product 1

HCID 13649254HCID 13649254, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

0.3 g of benzoyl chloride was slowly dropped onto 10 ml of a toluene solution containing 0.4 g of N-(α,α-dimethylbenzyl)-3-aminopropionamide (prepared as described in Preparation 3) and 0.22 g of triethylamine. The reaction solution was then stirred for 2 hours, and, after dilution with 20 ml of diethyl ether, was washed with water and dried over anhydrous sodium sulfate. The reaction solution was then concentrated by evaporation under reduced pressure, and purified by silica gel chromatography, to give 0.52 g (yield 87%) of the title compound melting at 147°-148° C.

Workup

  1. washafter dilution with 20 ml of diethyl ether, was washed with water
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationThe reaction solution was then concentrated by evaporation under reduced pressure
  4. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-4a2faaaa92b7401eb36c9c898aac16a5
Source dataset
uspto-grants-1990_02
Patent number
US04904680

Reaction notes

Loading…