Triphosgene → 2-(5,7-Dimethyl-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)-N,N-dimethylacetamide

HRID 656835Notes

Reaction equation

HRID 656835 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[NH:10][CH2:11][C:12]([N:14]([CH3:16])[CH3:15])=[O:13].Cl[C:18](Cl)([O:20]C(=O)OC(Cl)(Cl)Cl)Cl>>[CH3:8][C:6]1[CH:5]=[C:4]([CH3:9])[C:3]2[N:10]([CH2:11][C:12]([N:14]([CH3:16])[CH3:15])=[O:13])[C:18](=[O:20])[NH:1][C:2]=2[CH:7]=1

Participants

3

Reactant 2

HCID 94429TriphosgeneHCID 68997231N2-(2-Amino-4,6-dimethylphenyl)-N1,N1-dimethylglycinamide

Product 1

HCID 574571932-(5,7-Dimethyl-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)-N,N-dimethylacetamide

Procedure

To a solution of N2-(2-amino-4,6-dimethylphenyl)-N′,N′-dimethylglycinamide from Step B (930 mg, 4.20 mmol) in CH3 CN (20 mL) at 0° C. was added triphosgene (1.25 g, 4.20 mmol). The reaction mixture was stirred for 1 h, then quenched with H2O (50 mL) and extracted with CH2 Cl2 (3×50 mL). The combined organic layers were dried over Na2 SO4, filtered, and concentrated under reduced pressure. The crude product was purified by silica gel chromatography, eluting with a gradient of CH2 Cl2:MeOH—100:0 to 95:5, to give the title compound. MS: m/z=248 (M+1).

Workup

  1. customquenched with H2O (50 mL)
  2. extractionextracted with CH2 Cl2 (3×50 mL)
  3. customThe combined organic layers were dried over Na2 SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by silica gel chromatography
  7. washeluting with a gradient of CH2 Cl2

Sources & evidence

ORD record
ord-c4cf883222454de1b72f69354f450554
Source dataset
uspto-grants-2011_12
Patent number
US08071772B2

Reaction notes

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