Hydrochloric Acid → HCID 68733026, 화합물

HRID 341673

반응식

HRID 341673 반응식
[CH3:1][C:2]1([CH3:12])[C:7](=[O:8])[CH2:6][C:5](=[O:9])[C:4]([CH3:11])([CH3:10])[S:3]1.C(Cl)(Cl)Cl.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.[Br:29][C:30]1[CH:35]=[CH:34][C:33]([Pb+3])=[C:32]([CH2:37][CH3:38])[CH:31]=1.Cl>CN(C)C1C=CN=CC=1.C1(C)C=CC=CC=1>[Br:29][C:30]1[CH:35]=[CH:34][C:33]([CH:6]2[C:7](=[O:8])[C:2]([CH3:12])([CH3:1])[S:3][C:4]([CH3:11])([CH3:10])[C:5]2=[O:9])=[C:32]([CH2:37][CH3:38])[CH:31]=1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 6212ChloroformHCID 156501652,2,6,6-Tetramethylthiopyran-3,5-dioneHCID 178476529HCID 178476529, 화합물

생성물 1

HCID 68733026HCID 68733026, 화합물수율 40.9%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 1140Toluene용매

반응 조건

온도
80 °C

실험 절차

2,2,6,6-Tetramethylthiopyran-3,5-dione (10 g, 0.053 mol) (described in Helvetica Chimica Acta, 1992, 75(7), 2265-69) and 4-dimethylaminopyridine (32 g, 0.26 mol) are added to a mixture of chloroform (200 ml) and toluene (50 ml). The reaction mixture is flushed with nitrogen for 15 minutes at ambient temperature. 4-Bromo-2-ethylphenyllead triacetate (34 g, 0.06 mol) is added in one portion and the reaction mixture is stirred and heated to 80° C. (pre-heated oil bath) under an atmosphere of nitrogen for 1 hour. The reaction mixture is cooled to room temperature, acidified to pH 1 with 2N aqueous hydrochloric acid, filtered through a plug of diatomaceous earth and the two phases are separated. The aqueous phase is extracted with dichloromethane (2×100 ml). The organic phases are combined, washed with water, and dried over anhydrous sodium sulfate. The mixture is filtered, and the filtrate is evaporated under reduced pressure. The residue is purified by column chromatography on silica gel to give 4-(4-bromo-2-ethylphenyl)-2,2,6,6-tetramethylthiopyran-3,5-dione as a white solid (8 g).

후처리

  1. customThe reaction mixture is flushed with nitrogen for 15 minutes at ambient temperature
  2. temperature(pre-heated oil bath) under an atmosphere of nitrogen for 1 hour
  3. temperatureThe reaction mixture is cooled to room temperature
  4. filtrationfiltered through a plug of diatomaceous earth
  5. customthe two phases are separated
  6. extractionThe aqueous phase is extracted with dichloromethane (2×100 ml)
  7. washwashed with water
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationThe mixture is filtered
  10. customthe filtrate is evaporated under reduced pressure
  11. customThe residue is purified by column chromatography on silica gel

출처 및 근거

ORD 기록
ord-2c6339ad292648158a10cbb0d68069b5
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08895761B2

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