Acetonitrile → 1-(Triphenylmethyl)-1H-imidazole-4-carbonitrile

HRID 872914Notes

Reaction equation

HRID 872914 reaction equation
[C:1]1([C:7](Cl)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH:21]1[CH:25]=[C:24]([C:26]#[N:27])[N:23]=[CH:22]1.C(#N)C.C(N(CC)CC)C>O.CCCCCC>[C:7]([N:21]1[CH:25]=[C:24]([C:26]#[N:27])[N:23]=[CH:22]1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 6456Trityl chlorideHCID 8471TriethylamineHCID 178510437HCID 178510437, compound

Product 1

HCID 671686711-(Triphenylmethyl)-1H-imidazole-4-carbonitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8058HexaneSolvent

Procedure

Into a mixture containing triphenylmethyl chloride (1.647 g, 5.91 mmol), 1H-imidazole-4-carbonitrile (0.5 g, 5.37 mmol) and dry acetonitrile (17 ml), triethylamine (1.295 ml, 9.29 mmol) was added dropwise and the resulting mixture stirred overnight at RT. Hexane (1.6 ml) and water (17 ml) were poured into the mixture and the stirring was continued for another 30 min. The precipitate was filtered and dried with vacuum. 1H-NMR (400 MHz; CDCl3): δ 7.06-7.12 (m, 6H), 7.35-7.40 (m, 10H), 7.49 (d, 1H).

Workup

  1. additionwas added dropwise
  2. waitthe stirring was continued for another 30 min
  3. filtrationThe precipitate was filtered
  4. customdried with vacuum

Sources & evidence

ORD record
ord-dc7854c526c544e9bae4bbe0e1f852a1
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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