Tosylmethyl isocyanide → 1H-Imidazole, 1,5-diphenyl-

HRID 1023843ノート

反応式

HRID 1023843 の反応式
[CH:1](=[N:8]/[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)\[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC1C=CC(S([CH2:25][N+:26]#[C-:27])(=O)=O)=CC=1.C(O[Na])(C)(C)C>C1COCC1>[C:9]1([N:8]2[C:1]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[CH:27][N:26]=[CH:25]2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

参加物

5

反応物 3

HCID 161915Tosylmethyl isocyanideHCID 178418730sodium 2-methylpropan-2-olateHCID 178482110HCID 178482110、化合物

生成物 1

HCID 37706691H-Imidazole, 1,5-diphenyl-収率 18%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a stirred solution of (E)-N-benzylideneaniline (1.0 mmol) in THF (5 mL) was added TOSMIC (1.1 mmol) and t-BuONa (2.2 mmol). The solution was allowed to stir at room temperature for 5 days. The solvent was evaporated under reduced pressure and the crude product was absorbed on silica gel. After purification by flash column chromatography on silica gel the desired product was obtained in 18% yield. 1H NMR: 7.10-7.16 (m, 2H), 7.16-7.23 (m, 2H), 7.23-7.31 (m, 4H), 7.36-7.42 (m, 3H), 7.73 (s, 1H)

後処理

  1. customThe solvent was evaporated under reduced pressure
  2. customthe crude product was absorbed on silica gel
  3. customAfter purification by flash column chromatography on silica gel the desired product
  4. customwas obtained in 18% yield

出典と根拠

ORDレコード
ord-8431b24b409744afb48f099add971d42
出典データセット
uspto-grants-2014_05
特許番号
US08722720B2

反応ノート

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