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HCID 178428586, compound → HCID 178422297, compound

HRID 2064613
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Reaction equation

HRID 2064613 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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)+.

Workup

  1. custom
evaporated
  • customThe oily residue was partitioned between ethyl acetate and water
  • dry with materialThe organic layer was dried over magnesium sulfate
  • customevaporated
  • Sources & evidence

    ORD record
    ord-ade47eec0c4f46549c82711d752e0b6f
    Source dataset
    uspto-grants-2012_10
    DOI
    10.6084/m9.figshare.5104873.v1
    Patent number
    US08288425B2

    Reaction notes

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    On this pageParticipantsProcedureWorkupSources & evidenceReaction notes