N-bromobutanimide → 8-(5-Bromo-1,3-thiazol-2-yl)-1,4-dioxaspiro[4.5]decane-8-carbonitrile

HRID 410511노트

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HRID 410511 반응식
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1([C:16]#[N:17])[CH2:15][CH2:14][C:9]2([O:13][CH2:12][CH2:11][O:10]2)[CH2:8][CH2:7]1.[Br:18]N1C(=O)CCC1=O>CN(C=O)C>[Br:18][C:5]1[S:1][C:2]([C:6]2([C:16]#[N:17])[CH2:7][CH2:8][C:9]3([O:13][CH2:12][CH2:11][O:10]3)[CH2:14][CH2:15]2)=[N:3][CH:4]=1

참가 물질

4

반응물 2

HCID 67184N-bromobutanimideHCID 672567508-(1,3-Thiazol-2-yl)-1,4-dioxaspiro[4.5]decane-8-carbonitrile

생성물 1

HCID 672569798-(5-Bromo-1,3-thiazol-2-yl)-1,4-dioxaspiro[4.5]decane-8-carbonitrile수율 58.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
50 °C

실험 절차

To a solution of 8-(1,3-thiazol-2-yl)-1,4-dioxaspiro[4.5]decane-8-carbonitrile (1.78 g, 7.11 mmol) in anhydrous DMF (25 ml) was added N-bromosuccinimide (1.52 g, 8.53 mmol). The solution was heated at 50° C. for 2 h. The reaction was cooled to 23° C. then diluted with saturated aqueous NaS2O3 (175 ml) and extracted with EtOAc (2×130 ml). The combined organic layers were washed with brine (150 ml), dried over Na2SO4, filtered and concentrated. The crude yellow oil was purified via flash column chromatography (SiO2: 100% Hex to 60:40 Hex:EtOAc), to afford 8-(5-bromo-1,3-thiazol-2-yl)-1,4-dioxaspiro[4.5]decane-8-carbonitrile (1.43 g, 4.13 mmol, 58% yield) as an off-white solid. MS ESI: [M+H]+ m/z 331.1. 1H NMR (500 MHz, CDCl3): δ 7.66 (s, 1H), 4.01-3.93 (m, 4H), 2.39-2.26 (m, 4H), 2.07-2.01 (m, 2H), 1.88-1.86 (m, 2H).

후처리

  1. temperatureThe reaction was cooled to 23° C.
  2. extractionextracted with EtOAc (2×130 ml)
  3. washThe combined organic layers were washed with brine (150 ml)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude yellow oil was purified via flash column chromatography (SiO2: 100% Hex to 60:40 Hex:EtOAc)

출처 및 근거

ORD 기록
ord-b4f7e72bacde4454960c6eec02d7ab64
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08759366B2

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