Thionyl Chloride → HCID 59561810, compound

HRID 896341Notes

Reaction equation

[C:1]([O:5][C:6](=[O:25])[NH:7][CH2:8][C:9]1[CH:24]=[CH:23][C:12]2[N:13]([CH2:18][CH2:19][CH:20]([CH3:22])[CH3:21])[C:14]([CH2:16]O)=[N:15][C:11]=2[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].S(Cl)([Cl:28])=O>C(Cl)Cl>[C:1]([O:5][C:6](=[O:25])[NH:7][CH2:8][C:9]1[CH:24]=[CH:23][C:12]2[N:13]([CH2:18][CH2:19][CH:20]([CH3:22])[CH3:21])[C:14]([CH2:16][Cl:28])=[N:15][C:11]=2[CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

To a cooled (0° C.) solution of [2-hydroxymethyl-1-(3-methyl-butyl)-1H-benzoimidazol-5-ylmethyl]-carbamic acid tert-butyl ester (146 mg, 0.42 mmol) in DCM (5 mL) was added thionyl chloride (46 μL, 0.63 mmol). The solution was stirred at 0° C. for 15 min. and concentrated in vacuo to give [2-chloromethyl-1-(3-methyl-butyl)-1H-benzoimidazol-5-ylmethyl]-carbamic acid tert-butyl ester; HCl salt (176 mg, 100%) as a white solid, which was used without further purification.

Workup

concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-b2c49bbd95524e73ad2d24378976c321
Source dataset: uspto-grants-2005_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06919331B2

Reaction notes

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