Water → HCID 178514414, compound

HRID 1945489Notes

Reaction equation

HRID 1945489 reaction equation
C[O:2][C:3]([C:5]1[CH:23]=[CH:22][C:8]2[NH:9][C:10]([CH2:12][O:13][C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=3[Cl:21])=[N:11][C:7]=2[CH:6]=1)=O.O.[NH2:25][NH2:26].O>C(OCC)(=O)C>[Cl:21][C:15]1[CH:16]=[C:17]([Cl:20])[CH:18]=[CH:19][C:14]=1[O:13][CH2:12][C:10]1[NH:9][C:8]2[CH:22]=[CH:23][C:5]([C:3]([NH:25][NH2:26])=[O:2])=[CH:6][C:7]=2[N:11]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 178497368HCID 178497368, compound

Product 1

HCID 178514414HCID 178514414, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2-(2,4-dichloro-phenoxymethyl)-1H-benzoimidazole-5-carboxylic acid methyl ester (20 mg, 0.057 mmol) and hydrazine hydrate 0.2 ml was heated to reflux until reaction completion, then put cool water, diluted with ethyl acetate. The organic phase was separated, washed with brine and water, dried over anhydrous MgSO4. The resultant crude was filtered and concentrated under reduced pressure to afford 2-(2,4-dichloro-phenoxymethyl)-1H-benzoimidazole-5-carboxylic acid hydrazide as a solid (3 mg, 15% yield).

Workup

  1. temperatureto reflux until reaction completion
  2. customThe organic phase was separated
  3. washwashed with brine and water
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationThe resultant crude was filtered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f9d9901e3a864ac8bd0cef1fa60614eb
Source dataset
uspto-grants-2013_03
Patent number
US08394799B2

Reaction notes

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