Hydroxylamine → (NE)-N-[2-[8-[(4-methyl-2-propylbenzimidazol-1-yl)methyl]-6H-benzo[c][1]benzoxepin-11-ylidene]ethylidene]hydroxylamine

HRID 452166Notes

Reaction equation

HRID 452166 reaction equation
[CH3:1][C:2]1[C:10]2[N:9]=[C:8]([CH2:11][CH2:12][CH3:13])[N:7]([CH2:14][C:15]3[CH:32]=[CH:31][C:18]4/[C:19](=[CH:28]\[C:29]#[N:30])/[C:20]5[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=5[O:22][CH2:23][C:17]=4[CH:16]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1.N[OH:34].O>C(O)C>[CH3:1][C:2]1[C:10]2[N:9]=[C:8]([CH2:11][CH2:12][CH3:13])[N:7]([CH2:14][C:15]3[CH:32]=[CH:31][C:18]4[C:19](=[CH:28]/[CH:29]=[N:30]/[OH:34])[C:20]5[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=5[O:22][CH2:23][C:17]=4[CH:16]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 787HydroxylamineHCID 962WaterHCID 67210398(E)-2-{8-(4-methyl-2-propylbenzimidazol-1-yl)methyl-6,11-dihydrodibenzo[b,e]oxepin-11-ylidene}acetonitrile

Product 1

HCID 154041456(NE)-N-[2-[8-[(4-methyl-2-propylbenzimidazol-1-yl)methyl]-6H-benzo[c][1]benzoxepin-11-ylidene]ethylidene]hydroxylamineYield 93.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

[step 1] (E)-2-{8-(4-Methyl-2-propylbenzimidazol-1-yl)methyl-6,11-dihydrodibenzo[b,e]oxepin-11-ylidene}acetonitrile (310 mg, 0.74 mmol) obtained in Example 104, step 1 was dissolved in ethanol (3.7 mL), hydroxylamine (50% aqueous solution, 2.3 mL, 36.95 mmol) was added, and the mixture was stirred under reflux for 16 hr. Water was added to the mixture, and the precipitated solid was collected by filtration to give (E)-2-[8-(4-methyl-2-propylbenzimidazol-1-yl)methyl-6,11-dihydrodibenzo[b,e]oxepin-11-ylidene]acetaldoxime (304 mg, 91%). [step 2] Using (E)-2-[8-(4-methyl-2-propylbenzimidazol-1-yl)methyl-6,11-dihydrodibenzo[b,e]oxepin-11-ylidene]acetaldoxime (150 mg, 0.33 mmol) obtained in step 1 and in the same manner as in Example 107, the title compound (compound 108) (7.1 mg, 5%) was obtained.

Workup

  1. temperatureunder reflux for 16 hr
  2. filtrationthe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-81b0256bf7c24658a6bceaa43905dbff
Source dataset
uspto-grants-2013_07
Patent number
US08486980B2

Reaction notes

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