Diisopropyl Ether → 5-Methylbenzimidazolone

HRID 1503225Notes

Reaction equation

HRID 1503225 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4]([NH2:9])[CH:3]=1.[C:10](N1C=CN=C1)(N1C=CN=C1)=[O:11].C(OC(C)C)(C)C>O1CCCC1.ClCCl>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]2[NH:8][C:10](=[O:11])[NH:9][C:4]=2[CH:3]=1

Participants

6

Reactant 3

HCID 7914Diisopropyl EtherHCID 103323,4-DiaminotolueneHCID 682631,1'-Carbonyldiimidazole

Product 1

HCID 2231345-MethylbenzimidazoloneYield 81.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-methyl-1,2-phenylenediamine (1) (25 g) in tetrahydrofuran (375 mL) was added dropwise a solution of 1,1′-carbonyldiimidazole (36.5 g) in dichloromethane (375 mL). After stirring at room temperature for 6.5 hr, diisopropylether (375 mL) was added to the reaction mixture. After stirring at room temperature, the resulting precipitate was collected by filtration. The precipitate was washed with diisopropyl ether, and dried under reduced pressure to give 5-methyl-1,3-dihydrobenzimidazol-2-one (2) (24.6 g).

Workup

  1. stirringAfter stirring at room temperature
  2. filtrationthe resulting precipitate was collected by filtration
  3. washThe precipitate was washed with diisopropyl ether
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-5d4a4d46e4d341b2ad72b1f0468b94d1
Source dataset
uspto-grants-2015_12
Patent number
US09212169B2

Reaction notes

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