Acetyl chloride → 2-methyl-1-(tetrahydropyran-4-yl)benzimidazole-5-carboxylic acid HCl salt

HRID 74159

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[NH:11][CH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1)[C:5]([OH:7])=[O:6].[C:18]([Cl:21])(=O)[CH3:19].O1CCOCC1.Cl>O1CCOCC1>[ClH:21].[CH3:18][C:19]1[N:11]([CH:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[C:10]2[CH:9]=[CH:8][C:4]([C:5]([OH:7])=[O:6])=[CH:3][C:2]=2[N:1]=1

Participants

Conditions

Temperature: 10 °C

Procedure

3-Amino-4-((tetrahydropyran-4-yl)amino)benzoic acid (see Working Example 4-2) (90 g, 0.38 mol) was dissolved in dioxane (900 mL), and after cooling to 10° C., a solution of acetyl chloride (35.0 g, 0.45 mol) in dioxane (900 mL) was added dropwise over the course of 35 minutes. After heating to reflux with stirring for 2.5 h, another solution of acetyl chloride (15.8 g, 0.20 mol) in dioxane (200 mL) was added to the reaction solution, and this was further heated to reflux with stirring for 3 hours. Next, a 4N HCl dioxane solution (100 mL) was added, and after heating to reflux with stirring for 8 h, this was allowed to cool to room temperature, the solid obtained was filtered off and washed with hexane to yield the title compound (105 g, quant.) as a light purple solid.

Workup

temperatureAfter heating
temperatureto reflux
temperaturethis was further heated
temperatureto reflux
stirringwith stirring for 3 hours
temperatureafter heating
temperatureto reflux
stirringwith stirring for 8 h
temperatureto cool to room temperature
customthe solid obtained
filtrationwas filtered off
washwashed with hexane

Sources & evidence

ORD record: ord-c529147e2378423195e9ae0159b4dc6e
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08829035B2

Linked notes

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