Phthalimide → 2-(3-(phenylthio)propyl)-1H-isoindole-1,3(2H)-dione

HRID 2107123Notes

Reaction equation

HRID 2107123 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[C:13]1([S:19][CH2:20][CH2:21][CH2:22]O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:43]1(=[O:53])[NH:47][C:46](=[O:48])[C:45]2=[CH:49][CH:50]=[CH:51][CH:52]=[C:44]12>O1CCCC1>[C:13]1([S:19][CH2:20][CH2:21][CH2:22][N:47]2[C:43](=[O:53])[C:44]3[C:45](=[CH:49][CH:50]=[CH:51][CH:52]=3)[C:46]2=[O:48])[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 51558413-(Phenylsulfanyl)propan-1-ol

Product 1

HCID 2651852-(3-(phenylthio)propyl)-1H-isoindole-1,3(2H)-dioneYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diethyl azodicarboxylate (14 ml, 89 mmol) was added over 3 minutes to a stirred solution of 3-phenylthiopropanol (14.91 g, 89 mmol), triphenylphosphine (23.25 g, 89 mmol) and phthalimide (13.05 g, 89 mmol) in tetrahydrofuran (350 ml) at room temperature. After 15 hours, the mixture was concentrated in vacuo. Flash chromatography of the residue, eluting with 1:1 ether/hexane, gave the title compound as a white solid (22.5 g 85%). NMR (200 MHz, CDCl3): δ 2.0 (q, 2H), 2.95 (t, 2H), 3.85 (t, 2H), 7.25 (m, 5H), 7.8 (m, 4H).

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. washFlash chromatography of the residue, eluting with 1:1 ether/hexane

Sources & evidence

ORD record
ord-00f34f00c22b493a8d26f7a1f2502a40
Source dataset
uspto-grants-1990_06
Patent number
US04933369

Reaction notes

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