Toluene → HCID 21875544, compound

HRID 858462Notes

Reaction equation

HRID 858462 reaction equation
[Cl:1][C:2]1[C:22]([Cl:23])=[CH:21][C:5]2[N:6]([C:11]3[CH:16]=[CH:15][C:14]([CH2:17][C:18]([NH2:20])=[O:19])=[CH:13][CH:12]=3)[C:7]([CH2:9][CH3:10])=[N:8][C:4]=2[CH:3]=1.[C:24]1([CH3:36])[CH:29]=[CH:28][C:27]([S:30]([N:33]=[C:34]=[O:35])(=[O:32])=[O:31])=[CH:26][CH:25]=1.C1(C)C=CC=CC=1>C1COCC1>[Cl:1][C:2]1[C:22]([Cl:23])=[CH:21][C:5]2[N:6]([C:11]3[CH:12]=[CH:13][C:14]([CH2:17][C:18]([NH:20][C:34]([NH:33][S:30]([C:27]4[CH:28]=[CH:29][C:24]([CH3:36])=[CH:25][CH:26]=4)(=[O:32])=[O:31])=[O:35])=[O:19])=[CH:15][CH:16]=3)[C:7]([CH2:9][CH3:10])=[N:8][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 77703p-Toluenesulfonyl isocyanate2×HCID 21875557HCID 21875557, compound

Product 1

HCID 21875544HCID 21875544, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-[4-(5,6-dichloro-2-ethyl-1H-benzimidazol-1-yl)phenyl]acetamide (step 5, 105 mg, 0.30 mmol), p-toluenesulfonyl isocyanate (0.07 mL, 0.45 mmol), toluene (10 mL) and THF (5 mL) was heated at reflux temperature. After 6 h, an additional 0.1 mL of p-toluenesulfonyl isocyanate was added and the mixture was heated for 3 h. The mixture was cooled and left at room temperature for 2 days. The mixture was concentrated and the residue was purified by preparative TLC (ethyl acetate) to afford 150 mg (92%) of the title compound as colorless amorphous solids: 1H-NMR (CDCl3) δ 9.78 (1H, s), 7.95 (2H, d, J=8.3 Hz), 7.84 (1H, s), 7.54 (2H, d, J=8.4 Hz), 7.34 (2H, d, J=8.0 Hz), 7.32 (2H, d, J=8.4 Hz), 7.18 (1H, s), 3.78 (2H, s), 2.77 (2H, q, J=7.5 Hz), 2.41 (3H, s), 1.35 (3H, t, J=7.5 Hz).

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature
  3. temperaturethe mixture was heated for 3 h
  4. temperatureThe mixture was cooled
  5. waitleft at room temperature for 2 days
  6. concentrationThe mixture was concentrated
  7. customthe residue was purified by preparative TLC (ethyl acetate)

Sources & evidence

ORD record
ord-93df1d3b824a4fa4bdd01f7c956fbad5
Source dataset
uspto-grants-2006_12
Patent number
US07148234B2

Reaction notes

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