2-Methylbenzoyl chloride → HCID 178424296, compound

HRID 923353Notes

Reaction equation

HRID 923353 reaction equation
C(=O)(O)O.[NH:5]([C:7](=[NH:9])[NH2:8])[NH2:6].[CH3:10][C:11]1[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=1[C:13](Cl)=[O:14]>N1C=CC=CC=1>[CH3:10][C:11]1[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=1[C:13]([NH:6][NH:5][C:7](=[NH:8])[NH2:9])=[O:14]

Participants

4

Reactant 2

HCID 702762-Methylbenzoyl chlorideHCID 178513185HCID 178513185, compound

Product 1

HCID 178424296HCID 178424296, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of hydrazinecarboximidamide carbonic acid salt (12.0 g, 1.2 eq) in pyridine (100 mL) was added 2-methylbenzoyl chloride (crude afforded in step 1, 1.0 eq) dropwise at 0° C. The mixture was stirred overnight at room temperature. The reaction mixture was concentrated under vacuum, diluted with water (30 mL), adjusted to pH 12 with NaOH (aq), and the solid was collected by filtration and washed with water (20 mL) to afford 2-(2-methylbenzoyl)hydrazinecarboximidamide (5.0 g, 35% of two steps) as a white solid.

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. additiondiluted with water (30 mL)
  3. filtrationthe solid was collected by filtration
  4. washwashed with water (20 mL)

Sources & evidence

ORD record
ord-37c1ed0e9a7c4c639dbb36dfcb053595
Source dataset
uspto-grants-2016_03
Patent number
US09278973B2

Reaction notes

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