Hydrogen Bromide → 4-(1H-benzimidazol-2-yl)[1,4]diazepane hydriodic acid salt

HRID 2230513Notes

Reaction equation

HRID 2230513 reaction equation
C(OC([N:6]1[CH2:12][CH2:11][CH2:10][N:9]([C:13]2[NH:17][C:16]3[CH:18]=[CH:19][CH:20]=[CH:21][C:15]=3[N:14]=2)[CH2:8][CH2:7]1)=O)C.Br.[IH:23].O>C(O)C.C(OCC)C>[IH:23].[NH:14]1[C:15]2[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=2[N:17]=[C:13]1[N:9]1[CH2:10][CH2:11][CH2:12][NH:6][CH2:7][CH2:8]1

Participants

7

Reactant 4

HCID 260Hydrogen BromideHCID 962WaterHCID 24841Hydrogen iodideHCID 184650911-ethoxycarbonyl-4-(1H-benzimidazol-2-yl)[1,4]diazepane

Product 1

HCID 865838894-(1H-benzimidazol-2-yl)[1,4]diazepane hydriodic acid salt

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

Combine 1-ethoxycarbonyl-4-(1H-benzimidazol-2-yl)[1,4]diazepane (16.7 g, 58 mmol) and aqueous 48% hydrobromic acid solution (80 mL). Heat to reflux. After 3 hours, cool to ambient temperature, add to ethanol (700 mL), and cool to 0° C. to give a solid. Combine the solid with aqueous 48% hydriodic acid (80 mL) and water (150 mL). Heat on a steam bath. After about 1 hour, cool to ambient temperature, dilute with ethanol (500 mL), and add to diethyl ether (8 L) to give a solid. Collect solid by filtration and dry in vacuo to give the title compound: mp; >290° C.

Workup

  1. temperatureHeat to reflux
  2. temperaturecool to 0° C.
  3. customto give a solid
  4. temperatureHeat on a steam bath
  5. waitAfter about 1 hour
  6. temperaturecool to ambient temperature
  7. customto give a solid
  8. customCollect solid
  9. filtrationby filtration
  10. customdry in vacuo

Sources & evidence

ORD record
ord-6170ab396df84d739dfbe721a9388d74
Source dataset
uspto-grants-2002_07
Patent number
US06423704B1

Reaction notes

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