(R)-(-)-N-(2,3-Epoxypropyl)phthalimide → N-[(2R)-3-(1,3-benzothiazol-2-ylthio)-2-hydroxypropyl]-phthalimide

HRID 896633Notes

Reaction equation

HRID 896633 reaction equation
[O:1]1[CH2:3][C@H:2]1[CH2:4][N:5]1[C:9](=[O:10])[C:8]2=[CH:11][CH:12]=[CH:13][CH:14]=[C:7]2[C:6]1=[O:15].[SH:16][C:17]1[S:18][C:19]2[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=2[N:21]=1>CCO>[S:18]1[C:19]2[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=2[N:21]=[C:17]1[S:16][CH2:3][C@H:2]([OH:1])[CH2:4][N:5]1[C:9](=[O:10])[C:8]2=[CH:11][CH:12]=[CH:13][CH:14]=[C:7]2[C:6]1=[O:15]

Participants

4

Reactant 2

HCID 719415(R)-(-)-N-(2,3-Epoxypropyl)phthalimideHCID 178418395HCID 178418395, compound

Product 1

HCID 10109719N-[(2R)-3-(1,3-benzothiazol-2-ylthio)-2-hydroxypropyl]-phthalimideYield 59%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of compound N-[(2R)-oxiran-2-ylmethyl]-phthalimide (21.1 g, 104 mmol) and 2-mercaptobenzothiazole (17.4 g, 104 mmol) in EtOH (600 mL) was heated to reflux for 16.5 h. The reaction was then cooled and concentrated under reduced pressure. The crude mixture was crystallized from ethanol and filtered to provide N-[(2R)-3-(1,3-benzothiazol-2-ylthio)-2-hydroxypropyl]-phthalimide (22.5 g, 59%) as a yellow solid. Data for N-[(2R)-3-(1,3-benzothiazol-2-ylthio)-2-hydroxypropyl]-phthalimide: 1H NMR (300 MHz, CDCl3) δ 7.88 (m, 2H), 7.75 (m, 4H), 7.45-7.26 (m, 2H), 5.18 (m, 1H), 4.42 (m, 1H), 4.08-3.88 (m, 2H), 3.61 (m, 1H), 3.42 (m, 1H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 16.5 h
  3. temperatureThe reaction was then cooled
  4. concentrationconcentrated under reduced pressure
  5. customThe crude mixture was crystallized from ethanol
  6. filtrationfiltered

Sources & evidence

ORD record
ord-96dbfd0653a3425b944af13f4ba8c9ad
Source dataset
uspto-grants-2005_07
Patent number
US06919379B2

Reaction notes

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