Potassium Carbonate → N-[2-(1H-benzimidazol-2-yl)phenyl]propanamide

HRID 1439843Notes

Reaction equation

HRID 1439843 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[NH:9][C:10]2[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=2[N:12]=1.C(=O)([O-])[O-].[K+].[K+].[C:23](Cl)(=[O:26])[CH2:24][CH3:25]>C(#N)C>[NH:12]1[C:11]2[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=2[N:9]=[C:8]1[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[NH:1][C:23](=[O:26])[CH2:24][CH3:25]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 62324Propionyl chlorideHCID 798692-(1H-Benzimidazol-2-yl)aniline

Product 1

HCID 3378950N-[2-(1H-benzimidazol-2-yl)phenyl]propanamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution/suspension of 2-(2-aminophenyl) benzimidazole (5.0 g, 23.0 mmol), potassium carbonate (9.5 g, 69.0 mmol) in acetonitrile (300 mL) at 0° C. was added propionyl chloride (2.3 g, 23.0 mmol). The reaction mixture was allowed to warm to room temperature, stir overnight, followed by filtration to remove the white solid. This was washed thoroughly with acetonitrile. The acetonitrile was concentrated in vacuo, the residue extracted into methylene chloride, washed with potassium carbonate (saturated solution) and the organic layer was dried over anhydrous magnesium sulfate. The methylene chloride was removed in vacuo and the resulting solid was recrystallized from methanol, m.p. >200° C. 1H NMR (300 MHz, DMSO-d6) δ13.14 (bs, 1H), 13.00 (s, 1H), 8.70 (d, J=8.4 Hz, 1H), 8.10 (d, J=8.0 Hz, 1H), 7.71 (d, J=7.2 Hz, 1H), 7.57 (d, J=8.3 Hz, 1H), 7.46 (t, J=8.0 Hz, 1H), 7.31-7.20 (m, 3H), 2.53 (q, J=7.5 Hz, 2H), 1.23 (t, J=7.5 Hz, 313C NMR (75 MHz, DMSO-d6) δ172.2, 150.9, 172.1, 138.4, 133.4, 130.7, 127.3, 123.5, 122.7, 122.3, 119.8, 118.6, 115.2, 111.5, 31.1, 9.6; IR (KBr)3262, 1662 cm-1 ; MS (DCI) m/e MH+ =266; Analysis calc'd for C16H15N3O1 /0.4H2O1 : C, 70.53; H, 5.64; N, 15.37; H2O1, 2.40; found: C, 70.52; H, 5.84; N, 15.42; H2O1, 2.64.

Workup

  1. filtrationfollowed by filtration
  2. customto remove the white solid
  3. washThis was washed thoroughly with acetonitrile
  4. concentrationThe acetonitrile was concentrated in vacuo
  5. extractionthe residue extracted into methylene chloride
  6. washwashed with potassium carbonate (saturated solution)
  7. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  8. customThe methylene chloride was removed in vacuo
  9. customthe resulting solid was recrystallized from methanol, m.p. >200° C

Sources & evidence

ORD record
ord-651c1d5eda9d47aa8ac829296bb0afe7
Source dataset
uspto-grants-1996_03
Patent number
US05496826

Reaction notes

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