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

HRID 250490

반응식

HRID 250490 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 180Acetone용매HCID 962Water용매

실험 절차

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, 1.6 Hz, 1H), 4.40 (s, 2H), 4.21 (q, J=7.0 Hz, 2H), 3.37 (m, 1H), 2.07-1.28 (m, 13H).

후처리

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

출처 및 근거

ORD 기록
ord-8ac5c61566df40678a244d34121bd897
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07863292B2

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