Ethanol → HCID 86583899, compound

HRID 1584466Notes

Reaction equation

HRID 1584466 reaction equation
CO.ClCCl.C(OC([N:13]1[CH2:19][CH2:18][CH2:17][N:16]([C:20]2[N:24]([CH2:25][CH:26]=[CH2:27])[C:23]3[CH:28]=[CH:29][CH:30]=[CH:31][C:22]=3[N:21]=2)[CH2:15][CH2:14]1)=O)(C)(C)C.C(O)C.[IH:35]>C(OCC)C>[IH:35].[CH2:25]([N:24]1[C:23]2[CH:28]=[CH:29][CH:30]=[CH:31][C:22]=2[N:21]=[C:20]1[N:16]1[CH2:17][CH2:18][CH2:19][NH:13][CH2:14][CH2:15]1)[CH:26]=[CH2:27]

Participants

6

Reactant 4

HCID 702EthanolHCID 24841Hydrogen iodideHCID 184649651-(t-butoxycarbonyl)-4-(1-allyl-1H-benzimidazol-2-yl)[1,4]diazepaneHCID 21226129Dichloromethane methanol

Product 1

HCID 86583899HCID 86583899, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Combine 1-t-butoxycarbonyl-4-(1H-benzimidazol-2-yl)[1,4]diazepane (0.8 g, 2.5 mmol) in dimethylformamide (10 mL). Add sodium hydride (0.13 g, 60% in oil, 3.25 mmol). After about 30 minutes, when the gas evolution ceases, add allyl bromide (0.35 mL 4.0 mmol). Heat to 75° C. After 4 hours, dilute with ethyl acetate and extract with a saturated aqueous sodium bicarbonate solution and then brine. Dry the organic layer over MgSO4, filter, and evaporate in vacuo to give 1-t-butoxycarbonyl-4-(1-(allyl)-1H-benzimidazol-2-yl)[1,4]diazepane: Rf =0.83 (silica gel, 10% methanol/dichloromethane/0.1% concentrated aqueous ammonia). Combine 1-t-butoxycarbonyl-4-(1-(allyl)-1H-benzimidazol-2-yl)[1,4]diazepane (0.9 g, 2.5 mmol) and ethanol (10 mL). Add aqueous hydriodic acid (10 mL, 57%). Heat to reflux. After 1 hour, cool to ambient temperature and dilute with diethyl ether (250 mL) and stir to give a solid. Collect the solid by filtration, rinse with diethyl ether, and dry to give the title compound.

Workup

  1. temperatureHeat to reflux
  2. customto give a solid
  3. customCollect the solid
  4. filtrationby filtration
  5. washrinse with diethyl ether
  6. customdry

Sources & evidence

ORD record
ord-102a6a04cd52476bab758c7dea65623a
Source dataset
uspto-grants-1999_08
Patent number
US05932571

Reaction notes

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