Thionyl Chloride → HCID 70170438, compound

HRID 840775Notes

Reaction equation

S(Cl)([Cl:3])=O.[C:5]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:10]=[CH:9][C:8]([CH2:11][N:12]2[C:16]3[CH:17]=[C:18]([CH2:21]O)[CH:19]=[CH:20][C:15]=3[N:14]=[C:13]2[CH3:23])=[CH:7][CH:6]=1.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[C:5]1([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:6]=[CH:7][C:8]([CH2:11][N:12]2[C:16]3[CH:15]=[C:20]([Cl:3])[CH:19]=[C:18]([CH3:21])[C:17]=3[N:14]=[C:13]2[CH3:23])=[CH:9][CH:10]=1

Participants

Conditions

Temperature: 60 °C

Procedure

Thionyl chloride (2 ml) is added to a chloroform solution (30 ml) of 1-(biphenyl-4-ylmethyl)-6-hydroxymethyl-2-methylbenzimidazole (3.62 g), and the solution is stirred for one hour at 60° C. A sodium bicarbonate aqueous solution is added and the reaction is halted. The chloroform layer is washed with water and dried. After removing the solvent through evaporation under reduced pressure, ethyl acetate is added and crystallization is performed. After the crystals are separated through filtration and washed with ethyl acetate, they are dried and thus, 1-(biphenyl-4-ylmethyl)-6-chloro-methyl-2-methylbenzimidazole (2.04 g) is obtained. 1H-NMR (CDCl3, δ): 2.67 (3H, s), 4.71 (2H, s), 5.40 (2H. s), 7.12 (2H, d, J=8.2 Hz), 7.31-7.38 (3H, m), 7.43 (3, s), 7.52-7.58 (4H, m), 7.75 (1H, d, J=8.2 Hz).

Workup

washThe chloroform layer is washed with water
customdried
customAfter removing the solvent
customthrough evaporation under reduced pressure, ethyl acetate
additionis added
customcrystallization
customAfter the crystals are separated through filtration
washwashed with ethyl acetate, they
customare dried

Sources & evidence

ORD record: ord-faa512c2a7e04378b328e76e2f98c42d
Source dataset: uspto-grants-2002_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06369092B1

Reaction notes

Loading…