Hydrochloric Acid → HCID 178465628, compound

HRID 342850Notes

Reaction equation

HRID 342850 reaction equation
[C:1]([NH:9][C:10]1[CH:15]=[C:14]([C:16](=O)[CH3:17])[CH:13]=[C:12]([C:19](=O)[CH3:20])[CH:11]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:22]([NH:25][NH2:26])([NH2:24])=[NH:23].[ClH:27].Cl>C(O)C>[ClH:27].[ClH:27].[C:22]([NH:25][N:26]=[C:16]([C:14]1[CH:13]=[C:12]([C:19](=[N:26][NH:25][C:22](=[NH:23])[NH2:24])[CH3:20])[CH:11]=[C:10]([CH:15]=1)[NH:9][C:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH3:17])(=[NH:24])[NH2:23]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21195030HCID 21195030, compoundHCID 178418668HCID 178418668, compound

Product 1

HCID 178465628HCID 178465628, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Compound 26, FIG. 7E.26: A solution of 3,5-diacetylaniline (0.885 g) in tetrahydrofuran (10 mL) containing 0.45 mL pyridine was treated with 0.65 mL benzoyl chloride. The mixture was stirred 1 hr, then treated with 1 mL water and stirred 15 min. The mixture was then diluted with 40 mL water and stirred 30 min. Filtration and washing with water and isopropanol gave colorless needles of N-benzoyl-3,5-diacetylaniline, 1.36 g, mp 188°-189° C. A suspension of N-benzoyl-3,5-diacetylaniline (0.844 g) in aq. 87.5% ethanol (8 mL) containing 0.73 g aminoguanidine hydrochloride and a trace of HCl was heated at reflux for 18 hr. Cooling and filtration gave 1.357 g of N-benzoyl-3,5-diacetylaniline bis(amidinohydrazone)dihydrochloride (Compound 26), mp 268°-72° C.

Workup

  1. temperatureat reflux for 18 hr
  2. temperatureCooling
  3. filtrationfiltration

Sources & evidence

ORD record
ord-23c509f847c543c499e08a792494daac
Source dataset
uspto-grants-1999_01
Patent number
US05859062

Reaction notes

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