Dimethylformamide → S-[2-(1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl] ethanethioate

HRID 1731545Notes

Reaction equation

HRID 1731545 reaction equation
CC(C)([O-])C.[K+].CN(C)C=O.[C:12]([OH:15])(=[S:14])[CH3:13].Br[CH2:17][CH2:18][N:19]1[C:23](=[O:24])[C:22]2=[CH:25][CH:26]=[CH:27][CH:28]=[C:21]2[C:20]1=[O:29]>O>[C:12]([S:14][CH2:17][CH2:18][N:19]1[C:20](=[O:29])[C:21]2[C:22](=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:23]1=[O:24])(=[O:15])[CH3:13]

Participants

6

Reactant 4

HCID 6228Dimethylformamide3×HCID 113251H-Isoindole-1,3(2H)-dione, 2-(2-bromoethyl)-HCID 23665647Potassium tert-butoxideHCID 178418634HCID 178418634, compound

Product 1

HCID 120998S-[2-(1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl] ethanethioate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.855 kg (7.9M) Potassium-tert-butoxide is added in portions at -5° under nitrogen atmosphere to 4 1 dimethylformamide. A solution of 0.6 kg (7.9M) thioacetic acid in 2 1 dimethylformamide is added in a steady stream at such a rate that the temperature can be maintained between -5° and 0° . The reaction mixture is then stirred for 1 hour at -5° . 2.0 kg (7.9M) N-(2-bromoethyl)phthalimide in 4 1 dimethylformamide is added to the reaction mixture at such a rate that the temperature does not exceed 5° and the reaction mixture is stirred for 2 hours. 40 1 of water cooled at 5°-10° are added which raises the reaction temperature to 20° . The reaction mixture is stirred overnight at room temperature and filtered. The crude product is washed with water and dried. M.P. 112°-114°.

Workup

  1. temperaturecan be maintained between -5° and 0°
  2. customdoes not exceed 5°
  3. stirringthe reaction mixture is stirred for 2 hours
  4. additionare added which
  5. temperatureraises the reaction temperature to 20°
  6. stirringThe reaction mixture is stirred overnight at room temperature
  7. filtrationfiltered
  8. washThe crude product is washed with water
  9. customdried

Sources & evidence

ORD record
ord-ed8af05cff6448f9941a595d7cd8a214
Source dataset
uspto-grants-1986_11
Patent number
US04622322

Reaction notes

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