Pyridine → HCID 949996, compound

HRID 530299Notes

Reaction equation

HRID 530299 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.N1C=CC=CC=1.[CH3:16][N:17]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:18](Cl)=[O:19]>O1CCCC1>[CH3:16][N:17]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:18]([N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1)=[O:19]

Participants

5

Reactant 3

HCID 1049PyridineHCID 5798BenzimidazoleHCID 77969Carbamic chloride, N-methyl-N-phenyl-

Product 1

HCID 949996HCID 949996, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of 1H-benzo[d]imidazole (354 mg, 3 mmol) in tetrahydrofuran (15 ml) was added pyridine (0.367 ml, 4.50 mmol) followed by addition of methyl(phenyl)carbamic chloride (534 mg, 3.15 mmol). The reaction was heated to 80° C. for 20 hours. THF was removed by vacuum, the residue was partitioned between DCM and water. The organic phase was dried over MgSO4 and filtered. After evaporation the crude product was chromatographed in petroleum ether:EtOAc=2:1.

Workup

  1. customTHF was removed by vacuum
  2. customthe residue was partitioned between DCM and water
  3. dry with materialThe organic phase was dried over MgSO4
  4. filtrationfiltered
  5. customAfter evaporation the crude product
  6. customwas chromatographed in petroleum ether

Sources & evidence

ORD record
ord-05f8741f3a564a238f2fcfeab0f1cc15
Source dataset
uspto-grants-2016_05
Patent number
US09353082B2

Reaction notes

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