Cyclohexanecarbonyl chloride → HCID 57841372, compound

HRID 733638Notes

Reaction equation

[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:33]=[CH:32][C:16]([CH2:17][NH:18][C:19]3[CH:20]=[CH:21][C:22]4[C:27](=[O:28])[O:26][C:25]([CH3:30])([CH3:29])[O:24][C:23]=4[CH:31]=3)=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].[CH:34]1([C:40](Cl)=[O:41])[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1>>[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]([C:11]#[C:12][C:13]2[CH:33]=[CH:32][C:16]([CH2:17][N:18]([C:19]3[CH:20]=[CH:21][C:22]4[C:27](=[O:28])[O:26][C:25]([CH3:29])([CH3:30])[O:24][C:23]=4[CH:31]=3)[C:40]([CH:34]3[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]3)=[O:41])=[CH:15][CH:14]=2)=[CH:9][CH:10]=1)[CH2:2][CH2:3][CH3:4]

Participants

Reactant 2

HCID 75938Cyclohexanecarbonyl chloride

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

Product 1

HCID 57841372HCID 57841372, compound

Procedure

The titled compound was prepared following the procedure M using 7-({4-[(4-butylphenyl)ethynyl]benzyl}amino)-2,2-dimethyl-4H-1,3-benzodioxin-4-one and cyclohexanecarbonyl chloride as an orange oil (52%). 1H NMR (CDCl3, 300 MHz) δ 7.92 (d, J=8.3 Hz, 1H), 7.41 (m, 4H), 7.14 (m, 4H), 6.77 (m, 0.5H), 6.75 (m, 0.5H), 6.57 (m, 1H), 4.87 (s, 2H), 2.60 (t, J=7.5 Hz, 2H), 2.2 (m, 1H), 1.71 (s, 6H), 1.69-1.52 (m, 8H), 1.39-0.97 (m, 6H), 0.91 (t, J=7.3 Hz, 3H). M+ (ESI): 550.1. HPLC, Rt: 6.35 min (Purity: 97.5%).

Sources & evidence

ORD record: ord-664874e7cf5f49d1833ba9850c204c94
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07589232B2

Reaction notes

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