Ethyl Acetate → HCID 58156326, compound

HRID 1514912Notes

Reaction equation

HRID 1514912 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[NH:10][C:11]2[CH:17]=[C:16]([NH2:18])[CH:15]=[CH:14][C:12]=2[N:13]=1.[CH3:19][C:20]1[CH:21]=[C:22]([N:27]=[C:28]=[O:29])[CH:23]=[CH:24][C:25]=1[CH3:26].C(OCC)(=O)C>C1COCC1>[Cl:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[C:9]1[NH:10][C:11]2[CH:17]=[C:16]([NH:18][C:28]([NH:27][C:22]3[CH:23]=[CH:24][C:25]([CH3:26])=[C:20]([CH3:19])[CH:21]=3)=[O:29])[CH:15]=[CH:14][C:12]=2[N:13]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 43896633,4-Dimethylphenyl isocyanateHCID 28370697HCID 28370697, compound

Product 1

HCID 58156326HCID 58156326, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(2,6-dichlorophenyl)-3H-benzimidazol-5-ylamine (100 mg, 360 μmol) in THF (5 mL) was added 3,4-dimethylphenylisocyanate (51 μL, 54 mg., 360 μmols) and the mixture was stirred at ambient temperature for 18 h then was poured into ethyl acetate and extracted with water. The organic layer was dried, filtered, and solvent removed under reduced pressure to leave crude product that was purified by chromatography using a 50-90% gradient of heptane/ethyl acetate to give 1-[2-(2,6-dichlorophenyl)-3H-benzimidazol-5-yl]-3-(3,4-dimethylphenyl)-urea. 1H NMR (DMSO-d6, 400 MHz): δ 12.69 (s, broad, 1H), 8.69 (s, broad, 1H), 8.48 (s, 1H), 7.95 (s, broad, 1H), 7.67 (d, J=7.7 Hz, 2H), 7.60 (m, 2H), 7.26 (s, 1H), 7.20 (d, J=7.7 Hz, 1H) 7.03 (d, J=8.0 Hz, 2H), 2.20 (s, 3H), 2.16 (s, 3H); MS (m/z) 425.1 (M+1); Retention time=1.35 min (Method 10); High Resolution MS (M+1): theory 425.0936, measured 425.0951.

Workup

  1. extractionextracted with water
  2. customThe organic layer was dried
  3. filtrationfiltered
  4. customsolvent removed under reduced pressure
  5. customto leave crude product that
  6. customwas purified by chromatography

Sources & evidence

ORD record
ord-36f357baa32c42d2867a32babb23d2c4
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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