Aniline → N-phenylprop-2-ynamide
Reaction equation
[C:1](OC1C=CC(C2C=CC=CC=2)=CC=1)(=[O:4])[C:2]#[CH:3].[NH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(O)(=O)C#C.C1CCC(N=C=NC2CCCCC2)CC1>CN(C1C=CN=CC=1)C>[C:19]1([NH:18][C:1](=[O:4])[C:2]#[CH:3])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
The compound 20 was prepared according to the method described for compound 1 employing aniline (1 g, 0.01 mol), propargylic acid (0.76 g, 0.01 mol), DCC (2.2 g, 0.01) and DMAP (8.6 mg, 0.07 mmol) to give brown solid compound 20 (1.35 g, 87%). 1H NMR (300 MHz, CD2Cl2) δ 2.93 (s, 1H), 7.15 (t, J=6.9 Hz, 1H), 7.33 (t, J=7.5 Hz, 2H), 7.52 (t, J=7.4 Hz, 2H), 7.79 (br s, 1H).
Workup
- customThe compound 20 was prepared
Sources & evidence
- ORD record
- ord-a082bdbf594d4cd081cf7869750cc75a
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09393306B2
Reaction notes
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