Pyridine → HCID 21195030, compound

HRID 377040Notes

Reaction equation

HRID 377040 reaction equation
Cl.Cl.C(NN=C(C1C=C(C(=NNC(=N)N)C)C=C(C=1)N[C:16](=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)C)(=N)N.[C:32]([C:35]1[CH:36]=[C:37]([CH:39]=[C:40]([C:42](=[O:44])[CH3:43])[CH:41]=1)[NH2:38])(=[O:34])[CH3:33].N1C=CC=CC=1.C(Cl)(=O)C1C=CC=CC=1>O1CCCC1.O>[C:16]([NH:38][C:37]1[CH:39]=[C:40]([C:42](=[O:44])[CH3:43])[CH:41]=[C:35]([C:32](=[O:34])[CH3:33])[CH:36]=1)(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 7412Benzoyl chlorideHCID 463010Cni H1894HCID 178465628HCID 178465628, compound

Product 1

HCID 21195030HCID 21195030, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

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. stirringstirred 15 min
  2. stirringstirred 30 min
  3. filtrationFiltration
  4. washwashing with water and isopropanol

Sources & evidence

ORD record
ord-58c25a37c61648858535626aa1490f9b
Source dataset
uspto-grants-2000_02
Patent number
US06022900

Reaction notes

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