Water → 2H-Benzimidazol-2-one,1,3-dihydro-4,6-dimethyl-(9CI)

HRID 1675753Notes

Reaction equation

HRID 1675753 reaction equation
[CH3:1][C:2]1[CH:8]=[C:7]([CH3:9])[C:5]([NH2:6])=[C:4]([N+:10]([O-])=O)[CH:3]=1.Cl[C:14](Cl)([O:16]C(=O)OC(Cl)(Cl)Cl)Cl.O>CCO.[Pd]>[CH3:9][C:7]1[C:5]2[NH:6][C:14](=[O:16])[NH:10][C:4]=2[CH:3]=[C:2]([CH3:1])[CH:8]=1

Participants

6

Reactant 3

HCID 962WaterHCID 742196-Nitro-2,4-xylidineHCID 94429Triphosgene

Product 1

HCID 233544452H-Benzimidazol-2-one,1,3-dihydro-4,6-dimethyl-(9CI)

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 4,6-dimethyl-2-nitroaniline (10.0 g, 60.2 mmol) and 10% Pd/C (1.0 g) in EtOH (300 mL) was stirred under an atmosphere of hydrogen (ca. 1 atm) for 3 h, then filtered through a Celite pad and concentrated in vacuo. The crude solid was dissolved in CH3CN (200 mL) and triphosgene (15.0 g, 50.5 mmol) was added. The mixture was stirred for 1 h, then H2O (200 mL) was added slowly and stirring was continued for 1 h. The precipitate was isolated by filtration and dried to give the title compound. MS: m/z=163 (M+1).

Workup

  1. filtrationfiltered through a Celite pad
  2. concentrationconcentrated in vacuo
  3. dissolutionThe crude solid was dissolved in CH3CN (200 mL)
  4. stirringThe mixture was stirred for 1 h
  5. stirringstirring
  6. waitwas continued for 1 h
  7. customThe precipitate was isolated by filtration
  8. customdried

Sources & evidence

ORD record
ord-f91174161b3a4f00af2064b6bc818f81
Source dataset
uspto-grants-2011_08
Patent number
US08003792B2

Reaction notes

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