Pivaloyl chloride → N-{4-[(4-butylphenyl)ethynyl]benzyl}-N-(2,2-dimethyl-4-oxo-4H-1,3-benzodioxin-6-yl)-2,2-dimethylpropionamide

HRID 733555Notes

Reaction equation

Cl.[CH2:2]([C:6]1[CH:11]=[CH:10][C:9]([C:12]#[C:13][C:14]2[CH:34]=[CH:33][C:17]([CH2:18][NH:19][C:20]3[CH:32]=[CH:31][C:23]4[O:24][C:25]([CH3:30])([CH3:29])[O:26][C:27](=[O:28])[C:22]=4[CH:21]=3)=[CH:16][CH:15]=2)=[CH:8][CH:7]=1)[CH2:3][CH2:4][CH3:5].[CH3:35][C:36]([CH3:41])([CH3:40])[C:37](Cl)=[O:38]>>[CH2:2]([C:6]1[CH:7]=[CH:8][C:9]([C:12]#[C:13][C:14]2[CH:34]=[CH:33][C:17]([CH2:18][N:19]([C:20]3[CH:32]=[CH:31][C:23]4[O:24][C:25]([CH3:30])([CH3:29])[O:26][C:27](=[O:28])[C:22]=4[CH:21]=3)[C:37](=[O:38])[C:36]([CH3:41])([CH3:40])[CH3:35])=[CH:16][CH:15]=2)=[CH:10][CH:11]=1)[CH2:3][CH2:4][CH3:5]

Participants

Reactant 2

HCID 62493Pivaloyl chloride

HCID 684196986-({4-[(4-butylphenyl)ethynyl]benzyl}amino)-2,2-dimethyl-4H-1,3-benzodioxin-4-one hydrochloride

Product 1

HCID 57841357N-{4-[(4-butylphenyl)ethynyl]benzyl}-N-(2,2-dimethyl-4-oxo-4H-1,3-benzodioxin-6-yl)-2,2-dimethylpropionamide

Procedure

The titled compound was prepared following the procedure K using 6-({4-[(4-butylphenyl)ethynyl]benzyl}amino)-2,2-dimethyl-4H-1,3-benzodioxin-4-one hydrochloride and 2,2-dimethylpropanoyl chloride as a colorless oil (88%). 1H NMR (CDCl3, 300 MHz) δ 7.72 (d, J=2.5 Hz, 1H), 7.43 (m, 4H), 7.15 (m, 4H), 7.06 (dd, J=8.7, 2.5 Hz, 1H), 6.87 (d, J=8.7 Hz, 1H), 4.84 (s, 2H), 2.63 (t, J=7.7 Hz, 2H), 1.75 (s, 6H), 1.61 (m, 2H), 1.36 (m, 2H), 1.07 (s, 9H), 0.94 (t, J=7.4 Hz, 3H). M+ (ESI): 524.2. HPLC, Rt: 5.85 min (Purity: 99.5

Sources & evidence

ORD record: ord-bfc63ee949d64aa5a84fcbbeb943e219
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07589232B2

Reaction notes

Loading…