HCID 178428586, compound → HCID 178422297, compound

HRID 2182367Notes

Reaction equation

HRID 2182367 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([CH3:9])=[CH:4][C:3]=1[NH:10][C:11]([C:13]1[C:17]([N+:18]([O-:20])=[O:19])=[CH:16][NH:15][N:14]=1)=O>C(O)(=O)C>[CH3:9][C:5]1[C:6]([CH3:8])=[CH:7][C:2]2[NH:1][C:11]([C:13]3[C:17]([N+:18]([O-:20])=[O:19])=[CH:16][NH:15][N:14]=3)=[N:10][C:3]=2[CH:4]=1

Participants

3

Reactant 1

HCID 178428586HCID 178428586, compound

Product 1

HCID 178422297HCID 178422297, compoundYield 107%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A stirred solution of 4-nitro-1H-pyrazole-3-carboxylic acid (2-amino-4,5-dimethylphenyl)amide [5.7 g, Reference Example 36(a)] in acetic acid (100 mL) was heated at 120° C. for 1 hour, then cooled to ambient temperature and then evaporated. The oily residue was partitioned between ethyl acetate and water. The organic layer was dried over magnesium sulfate and then evaporated to give 5,6-dimethyl-2-(4-nitro-1H-pyrazol-3-yl)-1H-benzoimidazole (5.70 g) as an orange solid. LC-MS (METHOD B): RT=2.30 minutes, 258.11 (M+H)+. (b) 5-Ethyl-6-methyl-2-(4-nitro-1H-pyrazol-3-yl)-1H-benzoimidazole

Workup

  1. customevaporated
  2. customThe oily residue was partitioned between ethyl acetate and water
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-2c9cdbd007e945c0afd2a82ab9071ef8
Source dataset
uspto-grants-2005_05
Patent number
US06897208B2

Reaction notes

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