2-[(3-Chloro-2-chloromethyl-pyridin-4-yl)-methyl-amino]-ethanol → 2-{[2-(1H-benzimidazol-2-ylsulfanylmethyl)-3-chloropyridin-4-yl]-methylamino}-ethanol

HRID 1637623Notes

Reaction equation

[Cl:1][C:2]1[C:3]([CH2:13]Cl)=[N:4][CH:5]=[CH:6][C:7]=1[N:8]([CH3:12])[CH2:9][CH2:10][OH:11].[SH:15][C:16]1[NH:17][C:18]2[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=2[N:20]=1>CC(O)C>[NH:17]1[C:18]2[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=2[N:20]=[C:16]1[S:15][CH2:13][C:3]1[C:2]([Cl:1])=[C:7]([N:8]([CH3:12])[CH2:9][CH2:10][OH:11])[CH:6]=[CH:5][N:4]=1

Participants

Conditions

Temperature: 4 °C

Procedure

A solution of 2-[(3-chloro-2-chloromethyl-pyridin-4-yl)-methyl-amino]-ethanol isolated in step a) (10.2 g) and 2-mercapto-benzimidazole (5.8 g, 39 mmol) in 2-propanol (250 ml) is boiled under reflux for 2 h. After cooling to 4° C. the precipitate is filtered, washed with 2-propanol and dried in vacuo. The residue is dissolved in water, adjusted to pH 8 with aqueous sodium bicarbonate solution and extracted with ethyl acetate. The combined organic extracts are washed with water, dried over magnesium sulfate and evaporated in vacuo. The residue is crystallized from ethyl acetate to give the title compound as an off-white solid, 7.9 g (58%). M.p. 132-5° C.

Workup

temperatureunder reflux for 2 h
filtrationis filtered
washwashed with 2-propanol
customdried in vacuo
dissolutionThe residue is dissolved in water
extractionextracted with ethyl acetate
washThe combined organic extracts are washed with water
dry with materialdried over magnesium sulfate
customevaporated in vacuo
customThe residue is crystallized from ethyl acetate

Sources & evidence

ORD record: ord-ff0df0e4df0e4a9ea1b073210defe7f8
Source dataset: uspto-grants-2000_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06043242

Reaction notes

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