Tetrahydrofuran → 3-(4-Nitrobenzoyl)-1,3-thiazolidine-2-thione

HRID 1632248

반응식

HRID 1632248 반응식
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8](Cl)=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].O1CCCC1.[S:18]1[CH2:22][CH2:21][NH:20][C:19]1=[S:23]>C(N(CC)CC)C>[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([N:20]2[CH2:21][CH2:22][S:18][C:19]2=[S:23])=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2]

참가 물질

5

반응물 3

HCID 8028TetrahydrofuranHCID 85024-Nitrobenzoyl chlorideHCID 27236992-Thiazolidinethione

생성물 1

HCID 7723093-(4-Nitrobenzoyl)-1,3-thiazolidine-2-thione수율 73.6%

시약·촉매·용매 1

HCID 8471Triethylamine용매

반응 조건

온도
50 °C

실험 절차

To a solution of 4-nitrobenzoyl chloride (3.1 g) and tetrahydrofuran (50 ml) were added 1,3-thiazolidine-2-thione (2.0 g) and triethyl amine (2.5 g). The mixture was stirred at 50° C. for 30 minutes under nitrogen atmosphere. The reaction mixture was filtered and the solvent was removed at a reduced pressure. To the residue was added water, and the solution is extracted with dichloromethane. The extract was washed with a saturated aqueous solution of sodium chloride and dried with use of Glauber's salt. The solvent was distilled off and the resulting crystals were purified by silica gel column chromatography (developer: dichloromethane) and recrystallized from dichloromethane to obtain 3.3 g of the desired compound as yellow needle crystals (yield 82.5%).

후처리

  1. filtrationThe reaction mixture was filtered
  2. customthe solvent was removed at a reduced pressure
  3. additionTo the residue was added water
  4. extractionthe solution is extracted with dichloromethane
  5. washThe extract was washed with a saturated aqueous solution of sodium chloride
  6. dry with materialdried with use of Glauber's salt
  7. distillationThe solvent was distilled off
  8. customthe resulting crystals were purified by silica gel column chromatography (developer: dichloromethane)
  9. customrecrystallized from dichloromethane

출처 및 근거

ORD 기록
ord-c4d3668f304a4101990443742a0e5fe2
출처 데이터셋
uspto-grants-1984_10
특허 번호
US04474814

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