Pyridine → 5-(N-phenylcarbonyl-1,4-dihydro-4-pyridyl)-6-(4-fluorophenyl)-2,3-dihydroimidazo-[2,1-b]thiazole

HRID 1085246노트

반응식

HRID 1085246 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[N:14]([CH:15]=2)[CH2:13][CH2:12][S:11]3)=[CH:4][CH:3]=1.[N:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[C:22](Cl)(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(Cl)Cl>[C:23]1([C:22]([N:16]2[CH:21]=[CH:20][CH:19]([C:15]3[N:14]4[C:10]([S:11][CH2:12][CH2:13]4)=[N:9][C:8]=3[C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[CH:18]=[CH:17]2)=[O:29])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

참가 물질

5

반응물 3

HCID 1049PyridineHCID 7412Benzoyl chloride2회HCID 136398976-(4-Fluorophenyl)-2,3-dihydroimidazo[2,1-b][1,3]thiazole

생성물 1

HCID 144059635-(N-phenylcarbonyl-1,4-dihydro-4-pyridyl)-6-(4-fluorophenyl)-2,3-dihydroimidazo-[2,1-b]thiazole수율 81.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

6-(4-Fluorophenyl)-2,3-dihydroimidazo[2,1-b]thiazole (45.0 g, 0.204 mol) and 55 ml (0.68 mol) of pyridine were dissolved in 500 ml of methylene chloride To this cooled (ice-water bath) solution (10°) was added 91.3 g (0.65 mol) of benzoyl chloride in 100 ml of methylene chloride under a nitrogen atmosphere. During the addition, the reaction pot temperature was not allowed to rise past 10°. After the addition, the desired product precipitated from solution. The addition of the benzoyl chloride solution was continued. The resulting suspension was stirred at ambient temperature for 15 minutes, then heated to reflux for 15 minutes. Thin-layer chromatography (ethyl acetate/hexane/methanol, 15:1:0.1) showed the presence of some starting material. An additional 20 ml of pyridine followed by benzoyl chloride (28 g, 0.2 mol) were added at room temperature The suspension was stirred for an additional 0.5 hour. Analysis did not detect starting material at this time The reaction suspension was filtered. The collected solid was washed with petroleum ether. The solid was vacuum dried to yield 66.8 g (81%) of 5-(N-phenylcarbonyl-1,4-dihydro-4-pyridyl)6-(4-fluorophenyl)-2,3-dihydroimidazo-[2,1-b]thiazole; m.p. 188°-189°.

후처리

  1. additionDuring the addition
  2. customto rise past 10°
  3. additionAfter the addition
  4. customthe desired product precipitated from solution
  5. additionThe addition of the benzoyl chloride solution
  6. temperatureheated
  7. temperatureto reflux for 15 minutes
  8. additionwere added at room temperature The suspension
  9. stirringwas stirred for an additional 0.5 hour
  10. filtrationwas filtered
  11. washThe collected solid was washed with petroleum ether
  12. customdried

출처 및 근거

ORD 기록
ord-71cec2953c0042cd852569b1cc7b85a7
출처 데이터셋
uspto-grants-1991_04
특허 번호
US05008390

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