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

HRID 410511ノート

反応式

HRID 410511 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-b4f7e72bacde4454960c6eec02d7ab64
出典データセット
uspto-grants-2014_06
特許番号
US08759366B2

反応ノート

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