O,O-Diethyl dithiophosphate → 3-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)propanethioamide

HRID 1621098

Reaction equation

HRID 1621098 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][CH2:13][C:14]#[N:15].C(OP(=S)(OCC)[SH:20])C>O>[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][CH2:13][C:14]([NH2:15])=[S:20]

Participants

4

Reactant 2

HCID 9274O,O-Diethyl dithiophosphateHCID 3521693-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)propanenitrile

Product 1

HCID 9696783-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)propanethioamideYield 91%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A suspension of 3-(1,3-dioxoisoindolin-2-yl)-propionitrile (2 g, 9.99 mmol) and dithiophosphoric acid O,O′-diethyl ester (2.05 g, 1.74 mL, 11.0 mmol) in water (4 mL) was irradiated at 80° C. for 10 min. The obtained suspension was diluted with water (5 mL), filtered, washed with water and dried in vacuo to give the product as light yellow solid (2.13 g, 9.09 mmol, 91.0%) which was used without further purification for the next step. MS: M=235.1 (M+H)+

Workup

  1. customwas irradiated at 80° C. for 10 min
  2. filtrationfiltered
  3. washwashed with water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-3e555c6bb8984d90a54f7ba5a9148bbd
Source dataset
uspto-grants-2014_07
Patent number
US08772510B2

Linked notes

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