Tetrahydrofuran → 5-Methylbenzimidazolone

HRID 1096657Notes

Reaction equation

HRID 1096657 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH3:9])[CH:5]=[CH:6][C:7]=1[NH2:8].C1C[O:13][CH2:12]C1>>[CH3:9][C:4]1[CH:5]=[CH:6][C:7]2[NH:8][C:12](=[O:13])[NH:1][C:2]=2[CH:3]=1

Participants

3

Reactant 2

HCID 8028Tetrahydrofuran2×HCID 103323,4-Diaminotoluene

Product 1

HCID 2231345-MethylbenzimidazoloneYield 82%

Procedure

Into a 100 mL round bottomed flask, 3,4-diaminotoluene (1.00 g, 8.2 mmol) was dissolved in THF (8.2 mL). CDT (1.59 g, 9.8 mmol) in THF (25 mL) was added slowly via addition funnel. After addition the mixture was stirred overnight at room temperature. Solvent was removed under vacuum and the residue was purified by column chromatography (5% MeOH/DCM) to give the product 5-methyl-1H-benzo[d]imidazol-2(3H)-one (110A) as a brown-tan solid (990 mg, 82% yield). ESI-MS:m/z 149.4 (M+H)+.

Workup

  1. additionAfter addition the mixture
  2. customSolvent was removed under vacuum
  3. customthe residue was purified by column chromatography (5% MeOH/DCM)

Sources & evidence

ORD record
ord-04d014e3941942008cb6a4d14632d73e
Source dataset
uspto-grants-2012_03
Patent number
US08138168B1

Reaction notes

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