4-[2-(4-Butylphenyl)ethynyl]benzaldehyde → 7-[4-(4-Butyl-phenylethynyl)-benzylamino]-2,2-dimethyl-benzo[1,3]dioxin-4-one

HRID 733565Notes

Reaction equation

HRID 733565 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:20]=[CH:19][C:16]([CH:17]=O)=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].[NH2:21][C:22]1[CH:23]=[CH:24][C:25]2[C:30](=[O:31])[O:29][C:28]([CH3:33])([CH3:32])[O:27][C:26]=2[CH:34]=1>>[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:20]=[CH:19][C:16]([CH2:17][NH:21][C:22]3[CH:23]=[CH:24][C:25]4[C:30](=[O:31])[O:29][C:28]([CH3:32])([CH3:33])[O:27][C:26]=4[CH:34]=3)=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

3

Reactant 2

HCID 113345124-[2-(4-Butylphenyl)ethynyl]benzaldehydeHCID 231100727-Amino-2,2-dimethyl-4H-1,3-benzodioxine-4-one

Product 1

HCID 114192887-[4-(4-Butyl-phenylethynyl)-benzylamino]-2,2-dimethyl-benzo[1,3]dioxin-4-one

Procedure

The titled compound was prepared following the procedure A using 4-[(4-butylphenyl)ethynyl]benzaldehyde and 7-amino-2,2-dimethyl-4H-1,3-benzodioxin-4-one as a yellow powder (66%). 1H NMR (CDCl3, 300 MHz) δ 7.71 (d, J=8.6 Hz, 1H), 7.50 (d, J=8.3 Hz, 2H), 7.42 (d, J=8.3 Hz, 2H), 7.29 (d, J=8.3 Hz, 2H), 7.14 (d, J=7.9 Hz, 2H), 6.32 (m, 1H), 6.10 (m, 1H), 4.38 (s, 2H), 2.61 (t, J=7.7 Hz, 2H), 1.68 (s, 6H), 1.68-1.52 (m, 2H), 1.41-1.25 (m, 2H), 0.92 (t, J=7.3 Hz, 3H).

Sources & evidence

ORD record
ord-8ecfea4ff31c44b78ae0748a99cf5f40
Source dataset
uspto-grants-2009_09
Patent number
US07589232B2

Reaction notes

Loading…