Aniline → HCID 3300301, compound

HRID 1053519Notes

Reaction equation

HRID 1053519 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]=1

Participants

6

Reactant 4

HCID 6115AnilineHCID 10110Propiolic AcidHCID 10868DicyclohexylcarbodiimideHCID 10560973HCID 10560973, compound

Product 1

HCID 3300301HCID 3300301, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

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

  1. 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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