Toluene → HCID 178484390, compound

HRID 710495Notes

Reaction equation

HRID 710495 reaction equation
CO[CH:3](OC)[N:4]([CH3:6])[CH3:5].[NH:9]1[C:13]2[CH:14]=[CH:15][C:16]([C:18]([NH:20][NH2:21])=[O:19])=[CH:17][C:12]=2[N:11]=[CH:10]1.C1(C)C=CC=CC=1>CO>[CH3:6][N:4]([CH:3]=[N:21][NH:20][C:18]([C:16]1[CH:15]=[CH:14][C:13]2[NH:9][CH:10]=[N:11][C:12]=2[CH:17]=1)=[O:19])[CH3:5]

Participants

5

Reactant 3

HCID 1140TolueneHCID 78373Dimethylformamide dimethyl acetalHCID 178514415HCID 178514415, compound

Product 1

HCID 178484390HCID 178484390, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Dimethylformamide dimethyl acetal (19 g, 15.90 mmol) was added to a suspension of 1H-benzo[d]imidazole-5-carbohydrazide (3.50 g, 19.88 mmol) in 1:1 toluene; methanol (60 mL) and refluxed overnight. The volatiles were evaporated in vacuo to afford crude compound which was triturated with 6% methanol in chloroform (10 mL), precipitated solid was filtered and dried under reduced pressure to afford 3.20 g (69.56%%) 1H-benzimidazole-5-carboxylic acid dimethylaminomethylene-hydrazide as brown solid.

Workup

  1. customThe volatiles were evaporated in vacuo
  2. customto afford crude compound which
  3. customwas triturated with 6% methanol in chloroform (10 mL)
  4. customprecipitated solid
  5. filtrationwas filtered
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-b405c7f5540b48888292cab32b1b31c4
Source dataset
uspto-grants-2015_11
Patent number
US09181233B2

Reaction notes

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