Hydrochloric Acid → 5-Cyclohexylsulfanyl-isoindole-1,3-dione

HRID 1866441Notes

Reaction equation

HRID 1866441 reaction equation
[N+]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[NH:8][C:7]2=[O:14])([O-])=O.[CH:15]1([SH:21])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1.C(=O)([O-])[O-].[K+].[K+].Cl>CC(C)=O.O>[CH:15]1([S:21][C:4]2[CH:5]=[C:6]3[C:10](=[CH:11][CH:12]=2)[C:9](=[O:13])[NH:8][C:7]3=[O:14])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 69694-NitrophthalimideHCID 11430Potassium CarbonateHCID 15290Cyclohexanethiol

Product 1

HCID 667129985-Cyclohexylsulfanyl-isoindole-1,3-dioneYield 114.7%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A mixture of 5-nitro-isoindole-1,3-dione (10.0 g), cyclohexanethiol (9.1 g) and potassium carbonate (18.7 g) in acetone (260 ml) was heated to reflux overnight. After cooling, the mixture was diluted with water (250 ml) and then acidified by 6 N HCl to pH=4. Precipitate was collected and dried in vacuo to give the intermediate 5-cyclohexylsulfanyl-isoindole-1,3-dione (15.6 g). This intermediate was dissolved in acetone (170 ml) and to the mixture was added bromo ethylacetate (10.6 g) and potassium carbonate (23.8 g). The mixture was refluxed overnight. After cooling, reaction mixture was filtered and rinsed with ethyl acetate. Filtrate was concentrated and purified by silica gel chromatography (10%-50% ethyl acetate in methylene chloride) to give the title compound (13.1 g). 1H NMR (200 MHz, CDCl3) δ 7.73 (m, 2H), 7.56 (dd, J=7.8, 1.6Hz, 1H), 4.40 (s, 2H), 4.21 (q, J=7.0Hz, 2H), 3.37 (m, 1H), 2.07-1.28 (m, 13H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. temperatureAfter cooling
  4. customPrecipitate was collected
  5. customdried in vacuo

Sources & evidence

ORD record
ord-b4a867fe58c444f1b636dc1578dcc3f0
Source dataset
uspto-grants-2009_12
Patent number
US07629357B2

Reaction notes

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