1-(3-Ethoxy-4-methoxy-phenyl)-2-methanesulfonyl-ethylamine → HCID 9955212, compound

HRID 376378Notes

Reaction equation

HRID 376378 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].[CH3:19][N:20]([CH3:32])[C:21]1[CH:31]=[CH:30][CH:29]=[C:23]2[C:24]([O:26][C:27](=O)[C:22]=12)=[O:25]>C(O)(=O)C>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:12]([N:18]2[C:27](=[O:26])[C:22]3[C:23](=[CH:29][CH:30]=[CH:31][C:21]=3[N:20]([CH3:19])[CH3:32])[C:24]2=[O:25])[CH2:13][S:14]([CH3:17])(=[O:16])=[O:15])[CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH3:2]

Participants

4

Reactant 2

HCID 112887921-(3-Ethoxy-4-methoxy-phenyl)-2-methanesulfonyl-ethylamineHCID 127783133-Dimethylaminophthalic anhydride

Product 1

HCID 9955212HCID 9955212, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2-[1-(3-Ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-4-dimethylaminoisoindoline-1,3-dione was prepared by the procedure of Example 8 from 1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethylamine (572 mg, 2.09 mmol) and 3-dimethylaminophthalic anhydride (400 mg, 2.09 mmol) in acetic acid (20 mL). The product was obtained as a yellow solid (740 mg, 80% yield): mp, 94.0-96.0° C.; 1H NMR (CDCl3) δ 1.46 (t, J=7.0 Hz, 3H, CH3), 2.82 (s, 3H, CH3), 3.08 (s, 6H, CH3), 3.76-3.84 (m, 1H, CHH), 3.82 (s, 3H, CH3), 4.11 (q, J=7.0 Hz, 2H, CH2), 4.54 (dd, J=9.9, 14.5 Hz, 1H, CHH), 5.88 (dd, J=4.8, 9.9 Hz, 1H, NCH), 6.81-6.84 (m, 1H, Ar), 7.04-7.15 (m, 3H, Ar), 7.23-7.27 (m, 1H, Ar), 7.48 (dd, J=7.3, 8.3 Hz, 1H, Ar); 13C NMR (CDCl3) δ 14.68, 41.47, 43.39, 48.74, 55.20, 55.92, 64.43, 111.34, 112.54, 113.78, 114.41, 120.47, 122.09, 129.97, 134.32, 134.81, 148.46, 149.44, 150.42, 167.06, 168.19; Anal Calcd for C22H26NO6S: C, 59.14; H, 5.91; N, 6.27. Found: C, 59.14; H, 5.91; N, 6.10.

Sources & evidence

ORD record
ord-e31013ca662840bbb7d8831673ef3b96
Source dataset
uspto-grants-2000_02
Patent number
US06020358

Reaction notes

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