Benzil → HCID 178420035, compound

HRID 322018

Reaction equation

HRID 322018 reaction equation
[C:1]1([C:7]([C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=O)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH:17]([C:21]1[NH:22][C:23]2[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=2[N:25]=1)[C:18]([NH2:20])=[NH:19]>C1C=CC=CC=1.N1C=CC=CC=1>[N:25]1[C:24]2[CH:26]=[CH:27][CH:28]=[CH:29][C:23]=2[NH:22][C:21]=1[N:17]=[C:18]1[NH:20][C:7]2([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[NH:20][C:18](=[N:17][C:21]3[NH:25][C:24]4[CH:26]=[CH:27][CH:28]=[CH:29][C:23]=4[N:22]=3)[NH:19][C:9]2([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[NH:19]1

Participants

5

Reactant 2

HCID 8651BenzilHCID 1785125941-(1H-benzimidazol-2-yl)guanidine

Product 1

HCID 178420035HCID 178420035, compoundYield 17.8%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 1049PyridineSolvent

Procedure

A mixture of benzil (1.05 g, 5.0 mmol) and 2-guanidinobenzimidazole (1.57 g, 9.0 mmol) in benzene (25 mL) was refluxed in pyridine (10 mL) for 1 h. After evaporating most of the pyridine under reduced pressure, the residue was treated with hot toluene and the resulting precipitate was filtered. The precipitate was then dissolved in 9:1 water:acetic acid (30 mL); the solution was filtered and the filtrate was neutralized to pH 7 with phosphate buffer. A precipitate formed, that was then collected and triturated with water to afford the title compound (0.42 g, 16%). 1H NMR (300 MHz, d6-DMSO) d 11.5 (br s, NH, 2 H), 10.0 (br s, NH, 2 H), 8.6 (br s, NH, 2 H), 7.28-7.10 (m, 14 H), 6.97 (dd, J=6.0, 3.0 Hz, 4 H); MS (ESI) m/z 525 [M+H]+; Anal. Calcd. for C30H24N10 . ½CH3CO2H ¾H2O: C, 65.37; H, 4.88; N, 24.65. Found: C, 65.36; H, 4.79; N, 24.48.

Workup

  1. customAfter evaporating most of the pyridine under reduced pressure
  2. additionthe residue was treated with hot toluene
  3. filtrationthe resulting precipitate was filtered
  4. dissolutionThe precipitate was then dissolved in 9:1 water
  5. filtrationthe solution was filtered
  6. customA precipitate formed
  7. customthat was then collected
  8. customtriturated with water

Sources & evidence

ORD record
ord-0ff89d8a4ec7446ea87d3fe217c44e8c
Source dataset
uspto-grants-2001_04
Patent number
US06211200B1

Linked notes

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