Dichloromethane → HCID 18681138, compound

HRID 1699605Notes

Reaction equation

HRID 1699605 reaction equation
ClCCl.C(N(CC)CC)C.[C:11]([C:14]1[CH:15]=[CH:16][C:17]2[N:21]=[C:20]([CH2:22][CH2:23][CH3:24])[N:19]([CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[Cl:32])[C:18]=2[CH:33]=1)(=O)[NH2:12]>[Ti](Cl)(Cl)(Cl)Cl.O1CCCC1>[Cl:32][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=1[CH2:25][N:19]1[C:18]2[CH:33]=[C:14]([C:11]#[N:12])[CH:15]=[CH:16][C:17]=2[N:21]=[C:20]1[CH2:22][CH2:23][CH3:24]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 18680985HCID 18680985, compound

Product 1

HCID 18681138HCID 18681138, compound

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

Dichloromethane solution (1 molar, 0.14 ml) of titanium tetrachloride and triethylamine (0.36 ml) are added to a tetrahydrofuran solution (4 ml) of 6-carbamoyl-1-(2-chlorobenzyl)-2-n-propylbenzimidazole (200 mg) at 0 ° C., and the solution is stirred for two hours at 20° C. The reaction mixture is separated into layers using ethyl acetate and water. The organic layer is washed with water, dried and concentrated under reduced pressure. The residue is developed and purified using column chromatography with ethyl acetate/hexane (1/10˜1/3). The material is re-crystallized using ethyl acetate/hexane and 1-(2-chlorobenzyl)-6-cyano-2-n-propylbenzimidazole (140 ing) is obtained. (Colorless crystal) 1H-NMR (CDCl3, δ): 1.05 (3H, t, J=8 Hz), 1.90 (2H, sextet, J=8 Hz), 2.85 (2H, t, J=8 Hz), 5.45 (2H, s), 6.42, (1H, dd, J=1, 8 Hz), 7.15 (1H, dt, J=1, 8 Hz), 7.28 (1H, dt, J=1, 8Hz), 7.48 (1H, s), 7.50 (1H, d, J=10 Hz), 7.54 (1H, dd, J=1, 8 Hz), 7.85 (1H, d, J=10 Hz).

Workup

  1. customThe reaction mixture is separated into layers
  2. washThe organic layer is washed with water
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. custompurified
  6. customThe material is re-crystallized

Sources & evidence

ORD record
ord-ed2c14f598304a45a8f91be313685a97
Source dataset
uspto-grants-2002_02
Patent number
US06348032B1

Reaction notes

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