N,N-Diethylacrylamide → 4-Phenylcinnamic acid N,N-diethylamide

HRID 1156462

Reaction equation

HRID 1156462 reaction equation
[C:1]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:6]=[CH:5][C:4]([C:7](Cl)=O)=[CH:3][CH:2]=1.[CH2:16]([N:18]([CH2:23][CH3:24])[C:19](=[O:22])[CH:20]=C)[CH3:17]>>[CH2:16]([N:18]([CH2:23][CH3:24])[C:19](=[O:22])[CH:20]=[CH:7][C:4]1[CH:5]=[CH:6][C:1]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:2][CH:3]=1)[CH3:17]

Participants

3

Reactant 2

HCID 17583N,N-DiethylacrylamideHCID 841514-Phenylbenzoyl chloride

Product 1

HCID 541433974-Phenylcinnamic acid N,N-diethylamide

Conditions

Temperature
120 °C

Procedure

This compound is prepared from 10.83 g (50 millimols) of biphenyl-4-carboxylic acid chloride and 7.94 g (62.5 millimols) of N,N-diethylacrylamide, the mixture being stirred for 50 minutes at 120° C. The crude product is extracted, in a Soxhlet extractor, with 125 ml of n-hexane, and is recrystallised once from diethyl ether. 8.5 g (15% of theory) of pale yellow crystals, melting point 113.3° C., are obtained. Analysis for C10H21NO: calculated C 81.72%, H 7.53%, N 5.02%; found C 81.44%, H 7.50%, N 4.91%.

Workup

  1. extractionThe crude product is extracted, in a Soxhlet extractor, with 125 ml of n-hexane
  2. customis recrystallised once from diethyl ether
  3. custom8.5 g (15% of theory) of pale yellow crystals, melting point 113.3° C., are obtained

Sources & evidence

ORD record
ord-797fb9f8b8ee42a385393deccfc9c292
Source dataset
uspto-grants-1982_06
Patent number
US04335054

Linked notes

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