4-Nitrophthalic acid anhydride → HCID 9911513, compound

HRID 849243Notes

Reaction equation

HRID 849243 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:12]([NH2:18])[CH2:13][S:14]([CH3:17])(=[O:16])=[O:15])[CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH3:2].[N+:19]([C:22]1[CH:23]=[C:24]2[C:29](=O)[O:28][C:26](=[O:27])[C:25]2=[CH:31][CH:32]=1)([O-:21])=[O:20]>>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:12]([N:18]2[C:29](=[O:28])[C:24]3[C:25](=[CH:31][CH:32]=[C:22]([N+:19]([O-:21])=[O:20])[CH:23]=3)[C:26]2=[O:27])[CH2:13][S:14]([CH3:17])(=[O:16])=[O:15])[CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH3:2]

Participants

3

Reactant 2

HCID 2309764-Nitrophthalic acid anhydrideHCID 112887921-(3-Ethoxy-4-methoxy-phenyl)-2-methanesulfonyl-ethylamine

Product 1

HCID 9911513HCID 9911513, compoundYield 87%

Procedure

A stirred mixture of 1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethylamine (1.0 g, 3.7 mmol) and 4-nitrophthalic anhydride (706 mg, 3.66 mmol) was heated to melt for 6 min. The mixture was allowed to cool to room temperature. Chromatography of the resulting oil gave 2-[1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-5-nitro-iso-indoline-1,3-dione as a solid (1.42 g, 87% yield): mp, 255.0-256.0° C.; 1H NMR (CDCl3); δ 1.47 (t, J=7 Hz, 3H, CH3), 2.91 (s, 3H, CH3), 3.71 (dd, J=4.2, 14.3 Hz, 1H, CHH), 3.85 (2, 3H, CH3), 4.10 (q, J=7 Hz, 2H, CH2), 4.59 (dd, J=11.1, 14.1, Hz, 1H, CHH), 5.94 (dd, J=4.1, 10.9 Hz, 1H, NCH), 6.82-6.86 (m, 2H, Ar), 7.09-7.14 (m, 2H, Ar), 8.01-8.04 (m, 1H, Ar), 8.56-8.65 (m, 1H, Ar), 13C NMR (CDCl3) δ 14.67, 41.61, 49.16, 53.99, 55.96, 64.54, 111.48, 112.39, 118.98, 120.48, 124.79, 128.73, 129.39, 133.06, 136.03, 148.71, 149.92, 151.79, 165.56, 165.74; Anal Calcd for C20H20NO8S: C, 53.57; H, 4.50; N, 6.23. Found: C, 53.59; H, 4.58; N, 5.88.

Workup

  1. temperaturewas heated

Sources & evidence

ORD record
ord-c5cc93c1ea2c46d6b670824c41706063
Source dataset
uspto-grants-2000_01
Patent number
US06011050

Reaction notes

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