Phthalimide → Methyl-phenyl-carbamic Acid 4-[2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethyl]-phenyl Ester

HRID 1180074Notes

Reaction equation

HRID 1180074 reaction equation
O[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11](=[O:20])[N:12]([CH3:19])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:6][CH:5]=1.[C:21]1(=[O:31])[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:23](=[O:30])[NH:22]1>>[O:31]=[C:21]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:23](=[O:30])[N:22]1[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11](=[O:20])[N:12]([CH3:19])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:6][CH:5]=1

Participants

3

Reactant 2

HCID 6809PhthalimideHCID 69520342Methyl-phenyl-carbamic Acid 4-(2-hydroxy-ethyl)-phenyl Ester

Product 1

HCID 69518874Methyl-phenyl-carbamic Acid 4-[2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethyl]-phenyl EsterYield 39%

Procedure

The title compound was prepared in 39% yield as an oil using methyl-phenyl-carbamic acid 4-(2-hydroxy-ethyl)-phenyl ester and isoindole-1,3-dione. NMR (400 MHz; CDCl3): δ 2.98 (t, 2H), 3.41 (br s, 2H), 3.89 (t, 3H), 7.04 (br d, 2H), 7.20-7.40 (m, 7H), 7.68-7.71 (m, 2H), 7.80-7.83 (m, 2H); HPLC-MS: m/z=401.1 (M+1); Rt=4.41 min.

Sources & evidence

ORD record
ord-7a1ff448d29e45d28ecdb4bfd9ca933c
Source dataset
uspto-grants-2007_10
Patent number
US07279470B2

Reaction notes

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