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

HRID 1040002노트

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HRID 1040002 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-60cedf1f3a83412cbef9ad1848245cba
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08551984B2

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