1-(3-Ethoxy-4-methoxy-phenyl)-2-methanesulfonyl-ethylamine → 2-[1-(3-Ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-5-dimethylaminoisoindoline-1,3-dione
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:22]=[C:23]2[C:28](=O)[O:27][C:25](=[O:26])[C:24]2=[CH:30][CH:31]=1>C(O)(=O)C>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:12]([N:18]2[C:28](=[O:27])[C:23]3[C:24](=[CH:30][CH:31]=[C:21]([N:20]([CH3:19])[CH3:32])[CH:22]=3)[C:25]2=[O:26])[CH2:13][S:14]([CH3:17])(=[O:16])=[O:15])[CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH3:2]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
2-[1-(3-Ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-5-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 4-dimethylaminophthalic anhydride (400 mg, 2.09 mmol) in acetic acid (20 mL). The product was obtained as a yellow solid (200 mg, 21% yield): mp, 161.5-163.50° C.; 1H NMR (DMSO-d6) δ 1.46 (t, J=6.9 Hz, 3H, CH3), 2.79 (s, 3H, CH3), 3.09 (s, 6H, CH3), 3.78-3.85 (m, 1H, CHH), 3.85 (s, 3H, CH3), 4.11 (q, J=7.0 Hz, 2H, CH2), 4.51 (dd, J=9.7, 14.6 Hz, 1H, NCHH), 5.85 (dd, J=5.1, 9.6 Hz, AH, NCH), 6.75-6.84 (m, 2H, Ar), 7.03 (d, J=2.3 Hz, 1H, Ar), 7.10-7.16 (m, 2H, Ar), 7.61 (d, J=8.5 Hz, 1H, Ar), 13C NMR (DMSO-d6) δ 14.65, 40.40, 41.43, 48.83, 55.42, 55.89, 64.38, 105.80, 111.29, 112.43, 114.86, 116.90, 120.38, 125.11, 130.14, 134.27, 148.46, 149.38, 154.44, 168.14, 168.67; Anal Calcd for C22H26NO6S+0.2 H2O: C, 58.70; H, 5.91; N, 6.22. Found: C, 58.70; H, 5.93; N, 5.84.
Sources & evidence
- ORD record
- ord-7cea9bc925644b45aad45d08e893f8a3
- Source dataset
- uspto-grants-2000_02
- Patent number
- US06020358
Reaction notes
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