Water → Ethyl 4-[2-azido-4-chloro-7-(1-ethylpropyl)-1H-benzimidazol-1-yl]butanoate

HRID 1398792Notes

Reaction equation

Cl[C:2]1[N:6]([CH2:7][CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:5]2[C:15]([CH:20]([CH2:23][CH3:24])[CH2:21][CH3:22])=[CH:16][CH:17]=[C:18]([Cl:19])[C:4]=2[N:3]=1.[N-:25]=[N+:26]=[N-:27].[Na+].O>CN1CCCC1=O>[N:25]([C:2]1[N:6]([CH2:7][CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:5]2[C:15]([CH:20]([CH2:23][CH3:24])[CH2:21][CH3:22])=[CH:16][CH:17]=[C:18]([Cl:19])[C:4]=2[N:3]=1)=[N+:26]=[N-:27]

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of ethyl 4-[2,4-dichloro-7-(1-ethylpropyl)-1H-benzimidazol-1-yl]butanoate (Reference Example 33; 7.40 g, 20.0 mmol) and sodium azide (2.60 g, 40.0 mmol) in 1-methyl-2-pyrrolidinone (20 mL) was stirred at 110° C. for 12 hr. After cooling, water was added to the mixture, which was extracted with ethyl acetate. Organic layer was washed with water and brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatography on silica gel eluting with a 10-30% ethyl acetate/n-hexane gradient mixture. The filtrate was concentrated in vacuo to give the title compound (4.90 g, 12.9 mmol, 64%) as a pale yellow solid.

Workup

temperatureAfter cooling
extractionwas extracted with ethyl acetate
washOrganic layer was washed with water and brine
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated in vacuo
customThe residue was purified by flash chromatography on silica gel eluting with a 10-30% ethyl acetate/n-hexane gradient mixture
concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record: ord-a73bdc80e0b04111a1e9b281deba1239
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08901141B2

Reaction notes

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