Phosphorus oxychloride → HCID 52025964, compound

HRID 714312Notes

Reaction equation

HRID 714312 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=O)[C:10]1[CH:15]=[CH:14][N:13]=[C:12]([NH:16][C:17](=[O:24])[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:11]=1.P(Cl)(Cl)(Cl)=O>C1(C)C=CC=CC=1>[NH:8]1[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[N:1]=[C:9]1[C:10]1[CH:15]=[CH:14][N:13]=[C:12]([NH:16][C:17](=[O:24])[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:11]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 67153843HCID 67153843, compound

Product 1

HCID 52025964HCID 52025964, compoundYield 12%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of N-(2-aminophenyl)-2-benzamidoisonicotinamide (0.18 g, 0.53 mmol) in toluene (10 mL) was added phosphorus oxychloride (0.14 mL, 1.57 mmol) at ambient temperature. The resulting solution was refluxed for 5 hours, cooled to ambient temperature and concentrated in vacuo. The residue was taken up in 1 M aqueous sodium hydroxide solution (50 mL) and extracted with dichloromethane (2×50 mL). The combined organic layers were dried over anhydrous sodium sulphate, filtered and concentrated in vacuo to dryness. The residue was purified by column chromatography eluting with 20-100% ethyl acetate in hexanes to give N-(4-(1H-benzo[d]imidazol-2-yl)pyridin-2-yl)benzamide as a pale yellow solid (0.02 g, 9%): mp 145-146° C.; 1H NMR (300 MHz, DMSO-d6) δ 11.03 (s, 1H), 9.01 (s, 1H), 8.59 (d, J=5.2 Hz, 1H), 8.12-8.07 (m, 2H), 7.91 (dd, J=5.2, 1.4 Hz, 1H), 7.69 (dd, J=6.0, 3.2 Hz, 2H), 7.66-7.51 (m, 4H), 7.30 (dd, J=6.0, 3.2 Hz, 2H); MS (ES+) m/z 315.5 (M+1).

Workup

  1. temperatureThe resulting solution was refluxed for 5 hours
  2. concentrationconcentrated in vacuo
  3. extractionextracted with dichloromethane (2×50 mL)
  4. dry with materialThe combined organic layers were dried over anhydrous sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo to dryness
  7. customThe residue was purified by column chromatography
  8. washeluting with 20-100% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-ac30651dca344310855a0556cad6628b
Source dataset
uspto-grants-2015_11
Patent number
US09187426B2

Reaction notes

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