N-bromobutanimide → HCID 58095216, 화합물

HRID 1530135

반응식

HRID 1530135 반응식
C(O)[C@H]1O[C@@H]2O[C@H]3[C@H](O)[C@@H](O)[C@@H](O[C@H]4[C@H](O)[C@@H](O)[C@@H](O[C@H]5[C@H](O)[C@@H](O)[C@@H](O[C@H]6[C@H](O)[C@@H](O)[C@@H](O[C@H]7[C@H](O)[C@@H](O)[C@@H](O[C@H]8[C@H](O)[C@@H](O)[C@@H](O[C@H]1[C@H](O)[C@H]2O)O[C@@H]8CO)O[C@@H]7CO)O[C@@H]6CO)O[C@@H]5CO)O[C@@H]4CO)O[C@@H]3CO.[Cl:78][C:79]1[CH:84]=[C:83]([Cl:85])[CH:82]=[CH:81][C:80]=1[C:86](=O)[CH2:87][C:88]#[N:89].C1C(=O)N(Br)C(=O)C1.[NH2:99][C:100]([NH2:102])=[S:101]>O.CC(C)=O>[NH2:102][C:100]1[S:101][C:87]([C:88]#[N:89])=[C:86]([C:80]2[CH:81]=[CH:82][C:83]([Cl:85])=[CH:84][C:79]=2[Cl:78])[N:99]=1

참가 물질

7

반응물 4

HCID 67184N-bromobutanimideHCID 444041beta-CyclodextrinHCID 2723790ThioureaHCID 136307283-(2,4-Dichlorophenyl)-3-oxopropanenitrile

생성물 1

HCID 58095216HCID 58095216, 화합물수율 42%

시약·촉매·용매 2

HCID 180Acetone용매HCID 962Water용매

반응 조건

온도
50 °C

실험 절차

beta-Cyclodextrin (4.29 g, 3.78 mmol) was dissolved in water (75 mL) at 50° C. and a solution of 3-(2,4-dichlorophenyl)-3-oxopropanenitrile (810 mg, 3.8 mmol) in Acetone (3.80 mL) was added dropwise, followed by NBS (0.808 g, 4.54 mmol) and thiourea (0.346 g, 4.54 mmol). Reaction mixture was stirred at 50° C. 1 hr. LCMS indicated complete conversion. Reaction mixture was cooled to rt, extracted with ethyl acetate (3×50 mL), dried with MgSO4, filtered and concentrated under reduced pressure. The residue was purified by ISCO with 5-30% ethyl acetate in hexanes to give 0.43 g of the title compound (42%). LCMS; (FA) ES+, 270, 272, 1H NMR (400 MHz, d1-chloroform) δ 7.49 (d, J=1.84 Hz, 1H), 7.41 (d, J=8.30 Hz, 1H), 7.31 (dd, J=8.16, 1.74 Hz, 1H).

후처리

  1. customReaction mixture
  2. custom1 hr
  3. customReaction mixture
  4. temperaturewas cooled to rt
  5. extractionextracted with ethyl acetate (3×50 mL)
  6. dry with materialdried with MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by ISCO with 5-30% ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-91725012d7174cc38e98f48532a2f06c
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09090601B2

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