2,6-Lutidine → (2E)-N-(3-fluorophenyl)-3-phenyl-2-propenamide

HRID 255183Notes

Reaction equation

HRID 255183 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].[C:9](Cl)(=[O:18])[CH:10]=[CH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.N1C(C)=CC=CC=1C.BrC1C=C(NC(=O)/C=C/C2C=CC=CC=2)C=CC=1>>[F:1][C:2]1[CH:3]=[C:4]([NH:5][C:9](=[O:18])/[CH:10]=[CH:11]/[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 4

HCID 79372,6-LutidineHCID 97423-FluoroanilineHCID 660233-Phenylprop-2-enoyl chlorideHCID 874919(2E)-N-(3-bromophenyl)-3-phenylprop-2-enamide

Product 1

HCID 727184(2E)-N-(3-fluorophenyl)-3-phenyl-2-propenamide

Procedure

The compound was prepared from 3-fluoroaniline (5.8 mL, 60 mmol) and cinnamoylchloride (10 g, 60 mmol) in the presence of 2,6-lutidine (10.5 mL, 90 mmol) as described for Intermediate 18 to give a colorless solid, 13.9 g (96%), mp 110° C.

Workup

  1. customto give a colorless solid, 13.9 g (96%), mp 110° C.

Sources & evidence

ORD record
ord-e5b43bf397a24970984723678ea01866
Source dataset
uspto-grants-2011_01
Patent number
US07875715B2

Reaction notes

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