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Thionyl Chloride → HCID 18367388, 화합물

HRID 1741360
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HRID 1741360 반응식
O[CH2:2][CH2:3][CH2:4][CH:5]([NH:23][CH:24]1[C:33]2[C:28](=[C:29]([O:34][CH3:35])[CH:30]=[CH:31][CH:32]=2)[CH2:27][CH2:26][CH2:25]1)[C:6]1[O:7][C:8]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:10]=1.O=S(Cl)Cl>C(Cl)Cl>[C:11]1([C:9]2[N:10]=[C:6]([CH:5]3[CH2:4][CH2:3][CH2:2][N:23]3[CH:24]3[C:33]4[C:28](=[C:29]([O:34][CH3:35])[CH:30]=[CH:31][CH:32]=4)[CH2:27][CH2:26][CH2:25]3)[O:7][C:8]=2[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 2

HCID 24386Thionyl ChlorideHCID 18367346HCID 18367346, 화합물

생성물 1

HCID 18367388HCID 18367388, 화합물수율 65.9%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 1-[[4-hydroxy-1-(4,5-diphenyloxazol-2-yl)butyl]amino]-5-methoxy-1,2,3,4-tetrahydronaphthalene (0.9 g) in CH2Cl2 (20 ml) was added SOCl2 (3 ml). After being stirred for 4 hours, the solvent was removed. The residue was dissolved in CH3CN (20 ml) and K2CO3 (5 g) was added to the solution. After being stirred for 4 hours under reflux, the solution was poured into the mixture of ethyl acetate and water. The organic layer was washed with water and brine, dried over MgSO4, and evaporated in vacuo. The residue was purified by chromatography on silica gel to afford 1-[2-(4,5-diphenyloxazol-2-yl)pyrrolidin-1-yl]-5-methoxy-1,2,3,4-tetrahydronaphthalene (0.57 g). MS (m/z): 451 (M+ +1) IR (Neat): 1580 cm-1NMR (CDCl3, δ): 1.5-2.3 (8H, m), 2.4-3.2 (4H, m), 3.69 and 3.76 (3H, each s), 4.0-4.2 (2H, m), 6.4-6.72 (3H, m), 7.3-7.7 (10H, m)

후처리

  1. customthe solvent was removed
  2. dissolutionThe residue was dissolved in CH3CN (20 ml)
  3. additionK2CO3 (5 g) was added to the solution
  4. stirringAfter being stirred for 4 hours
  5. temperatureunder reflux
  6. additionthe solution was poured into the mixture of ethyl acetate and water
  7. washThe organic layer was washed with water and brine
  8. dry with materialdried over MgSO4
  9. customevaporated in vacuo
  10. customThe residue was purified by chromatography on silica gel

출처 및 근거

ORD 기록
ord-247ef4999efe452ba43850071356d048
출처 데이터셋
uspto-grants-1999_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05972965

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