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

HRID 1023843Notes

Reaction equation

HRID 1023843 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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)

Workup

  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

Sources & evidence

ORD record
ord-8431b24b409744afb48f099add971d42
Source dataset
uspto-grants-2014_05
Patent number
US08722720B2

Reaction notes

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