3-Dimethylaminophthalic anhydride → HCID 9957064, compound

HRID 376384Notes

Reaction equation

HRID 376384 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:15]([NH2:21])[CH2:16][S:17]([CH3:20])(=[O:19])=[O:18])[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:22][N:23]([CH3:35])[C:24]1[CH:34]=[CH:33][CH:32]=[C:26]2[C:27]([O:29][C:30](=O)[C:25]=12)=[O:28]>C(O)(=O)C>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:15]([N:21]3[C:30](=[O:29])[C:25]4[C:26](=[CH:32][CH:33]=[CH:34][C:24]=4[N:23]([CH3:22])[CH3:35])[C:27]3=[O:28])[CH2:16][S:17]([CH3:20])(=[O:18])=[O:19])[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 2

HCID 127783133-Dimethylaminophthalic anhydrideHCID 54161446HCID 54161446, compound

Product 1

HCID 9957064HCID 9957064, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2-[1-(3-Cyclopentyloxy-4-methoxyphenyl)-2-methylsulfonylethyl]-4-dimethylaminoisoindoline-1,3-dione was prepared by the procedure of Example 8 from 1-(3-Cyclopentyloxy-4-methoxyphenyl)-2-methylsulfonylethylamine (1.0 g, 3.18 mmol) and 3-dimethylaminophthalic anhydride (608 mg, 3.18 mmol) in acetic acid (10 mL). The product was obtained as a yellow solid (780 mg, 50% yield): mp, 192.0-194.0° C.; 1H NMR (CDCl3) δ 1.61-1.64 & 1.82-2.00 (2 m's, 8H, C5H8), 2.79 (s, 3H, CH3), 3.08 (s, 6H, CH3), 3.81 (s, 3H, CH3), 3.82 (dd, J=5.5, 14.5 Hz, 1H, CHH), 4.52 (dd, J=9.8, 14.5 Hz, 1H, CHH), 4.75-4.81 (m, 1H, OCH), 5.87 (dd, J=5.0, 9.7 Hz, 1H, NCH), 6.80 (d, J=8.3 Hz, 1H, Ar), 7.03-7.26 (m, 3H, Ar), 7.47 (dd, J=7.3, 8.4 Hz, 1H, Ar); 13C NMR (CDCl3) δ 24.05, 32.75, 41.47, 43.37, 48.84, 55.36, 56.02, 80.55, 111.88, 113.74, 114.46, 114.71, 120.41, 122.04, 129.88, 134.39, 134.77, 147.91, 150.22, 150.39, 167.05, 168.13; Anal Calcd for C25H30N2O6S: C, 61.71; H, 6.21; N, 5.76. Found: C, 61.58; H, 6.06; N, 5.53.

Sources & evidence

ORD record
ord-1b2e2c3bd3c64512850b90abde251929
Source dataset
uspto-grants-2000_02
Patent number
US06020358

Reaction notes

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