(S)-(+)-N-(2,3-Epoxypropyl)phthalimide → HCID 10270502, compound

HRID 896632Notes

Reaction equation

HRID 896632 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 719412(S)-(+)-N-(2,3-Epoxypropyl)phthalimideHCID 178418395HCID 178418395, compound

Product 1

HCID 10270502HCID 10270502, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of N-[(2S)-oxiran-2-ylmethyl]-phthalimide (18.4 g, 90.6 mmol) and 2-mercaptobenzothiazole (15.8 g, 94.5 mmol) in EtOH (530 mL) was heated to reflux for 14.5 h. The reaction was then cooled and concentrated under reduced pressure. The crude mixture was crystallized from ethanol and filtered to provide N-[(2S)-3-(1,3-benzothiazol-2-ylthio)-2-hydroxypropyl]-phthalimide (25.5 g, 76%) as a solid. Data for N-[(2S)-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), 5.15 (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 14.5 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-1fec46728a274374ba0f40c08df2c992
Source dataset
uspto-grants-2005_07
Patent number
US06919379B2

Reaction notes

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