4-[(4-Chlorophenyl)ethynyl]benzaldehyde → 6-({4-[(4-chlorophenyl)ethynyl]benzyl}amino)-2,2-dimethyl-4H-1,3-benzodioxin-4-one

HRID 733603Notes

Reaction equation

HRID 733603 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][C:10]2[CH:17]=[CH:16][C:13]([CH:14]=O)=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.[NH2:18][C:19]1[CH:31]=[CH:30][C:22]2[O:23][C:24]([CH3:29])([CH3:28])[O:25][C:26](=[O:27])[C:21]=2[CH:20]=1>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][C:10]2[CH:17]=[CH:16][C:13]([CH2:14][NH:18][C:19]3[CH:31]=[CH:30][C:22]4[O:23][C:24]([CH3:28])([CH3:29])[O:25][C:26](=[O:27])[C:21]=4[CH:20]=3)=[CH:12][CH:11]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 112534834-[(4-Chlorophenyl)ethynyl]benzaldehydeHCID 116153306-Amino-2,2-dimethyl-benzo[1,3]dioxin-4-one

Product 1

HCID 111543016-({4-[(4-chlorophenyl)ethynyl]benzyl}amino)-2,2-dimethyl-4H-1,3-benzodioxin-4-one

Procedure

The titled compound was prepared following the procedure A using 4-[(4-chlorophenyl)ethynyl]benzaldehyde (intermediate which may be obtained according to methods disclosed in EP03103780.7) and 6-amino-2,2-dimethyl-4H-1,3-benzodioxin-4-one as a yellow powder (62%). 1H NMR (CDCl3, 300 MHz) δ 7.52-7.41 (m, 4H), 7.38-7.28 (m, 4H), 7.16 (d, J=2.7 Hz, 1H), 6.87-6.76 (m, 2H), 4.34 (s, 2H), 1.68 (s, 6H). M− (ESI): 416.1. HPLC, Rt: 5.45 min (Purity: 96%).

Sources & evidence

ORD record
ord-b51d6328df684a4bb7307672ac86b65d
Source dataset
uspto-grants-2009_09
Patent number
US07589232B2

Reaction notes

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