L-Alanine → HCID 69585481, compound

HRID 1828195Notes

Reaction equation

HRID 1828195 reaction equation
[CH2:1]([N:3]1[C:7]2[CH:8]=[CH:9][C:10]([CH:12]=O)=[CH:11][C:6]=2[N:5]([CH2:14]C)[C:4]1=[O:16])C.N[C@H](C(O)=O)C.[N+:23]([CH2:26][CH3:27])([O-:25])=[O:24]>C(O)CCC>[CH3:1][N:3]1[C:7]2[CH:8]=[CH:9][C:10]([CH:12]=[C:26]([N+:23]([O-:25])=[O:24])[CH3:27])=[CH:11][C:6]=2[N:5]([CH3:14])[C:4]1=[O:16]

Participants

5

Reactant 3

HCID 5950L-AlanineHCID 6587Nitroethane2×HCID 64841051,3-Diethyl-2-oxo-2,3-dihydro-1H-benzoimidazole-5-carbaldehyde

Product 1

HCID 69585481HCID 69585481, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
115 °C

Procedure

1,3-Dimethyl-2-oxo-2,3-dihydro-1H-benzoimidazole-5-carbaldehyde (2.48 g, 13.1 mmol, obtained using the same procedure used for 1,3-Diethyl-2-oxo-2,3-dihydro-1H-benzoimidazole-5-carbaldehyde) in n-butanol (25 mL) was treated with □-alanine (298.0 mg) and nitroethane (1.85 mL). The mixture was heated to 115° C. for 4 hours, more nitroethane (0.5 mL) was added and the heating was continued for 2 hours. The reaction was allowed to cool, was filtered and washed with ether then dried to give 1,3-Dimethyl-5-(2-nitro-propenyl)-1,3-dihydro-benzoimidazol-2-one (2.229 g).

Workup

  1. temperatureto cool
  2. filtrationwas filtered
  3. washwashed with ether
  4. customthen dried

Sources & evidence

ORD record
ord-44481c2101274dcaa188306f9db1e86e
Source dataset
uspto-grants-2006_06
Patent number
US07056918B2

Reaction notes

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