3,4-Diaminobenzophenone → HCID 178439943, compound

HRID 1595308Notes

Reaction equation

HRID 1595308 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][C:15]=1[NH2:16])[C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:6].Cl.[C:18](=N)(OCC)[CH2:19][CH2:20][CH3:21]>C(O)C>[C:7]1([C:5]([C:4]2[CH:13]=[CH:14][C:15]3[NH:16][C:18]([CH2:19][CH2:20][CH3:21])=[N:1][C:2]=3[CH:3]=2)=[O:6])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 1355203,4-DiaminobenzophenoneHCID 12235055Ethyl butyrimidate hydrochloride

Product 1

HCID 178439943HCID 178439943, compoundYield 45.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3,4 diaminobenzophenone (21.2 g; 0.1 mol) and ethyl butyrimidate hydrochloride (22.7 g; 0.15 mol) in ethanol (500 mL) was heated at reflux for a period of 6 hours. The mixture was stirred at ambient temperature for 18 hours. The solvent was evaporated and the residue was purified by flash chromatography on silica gel (EtOAc/Hexane; 1:1). Crystallization from ethyl acetate provided 12 g (45% yield) of the title compound as an off-white solid, m.p. 131-132° C. Anal. Calcd. for C17H16N2O: C, 77.25; H, 6.10; N, 10.60. Found: C, 77.20; H, 6.06; N, 10.72. Mass spectrum (EI; M+) m/z 264. 1H-NMR (DMSO-d6; 400 MHz) δ12.56 (br s, 1H), 7.84 (s, 1H), 7.73 (m, 2H), 7.65 (m, 1H), 7.60 (s, 2H), 7.56 (t, 2H), 2.82 (t, 2H), 1.80 (m, 2H), and 0.95 ppm (t, 3H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for a period of 6 hours
  3. customThe solvent was evaporated
  4. customthe residue was purified by flash chromatography on silica gel (EtOAc/Hexane; 1:1)
  5. customCrystallization from ethyl acetate

Sources & evidence

ORD record
ord-65f9c9d658e248f49f38bf24d76ab7c3
Source dataset
uspto-grants-2001_09
Patent number
US06288100B1

Reaction notes

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