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

HRID 1023843노트

반응식

HRID 1023843 반응식
[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

참가 물질

5

반응물 3

HCID 161915Tosylmethyl isocyanideHCID 178418730sodium 2-methylpropan-2-olateHCID 178482110HCID 178482110, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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)

후처리

  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

출처 및 근거

ORD 기록
ord-8431b24b409744afb48f099add971d42
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08722720B2

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