Isopropanol → HCID 178518642, compound

HRID 631942Notes

Reaction equation

HRID 631942 reaction equation
[Br:1][C:2]1[C:3]([CH:11]=O)=[CH:4][C:5]2[O:9][CH2:8][O:7][C:6]=2[CH:10]=1.CC(O)C.[NH2:17][C:18]1[CH:27]=[CH:26][C:21]2[NH:22][C:23](=[O:25])[NH:24][C:20]=2[CH:19]=1>C(O)(=O)C>[Br:1][C:2]1[C:3](/[CH:11]=[N:17]/[C:18]2[CH:27]=[CH:26][C:21]3[NH:22][C:23](=[O:25])[NH:24][C:20]=3[CH:19]=2)=[CH:4][C:5]2[O:9][CH2:8][O:7][C:6]=2[CH:10]=1

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 667655-Amino-2-hydroxybenzimidazoleHCID 950621,3-Benzodioxole-5-carboxaldehyde, 6-bromo-

Product 1

HCID 178518642HCID 178518642, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

6-bromobenzo[d][1,3]dioxol-5-carbaldehyde (0.63 g, 1.31 mmol), IPA (6 ml), and 5-amino-1H-benzo[d]imidazole-2(3H)-one (0.2 g, 1.31 mmol) were put in a 25 ml flask, and acetic acid (10 ml) was slowly added dropwise thereto while the mixture was stirred under nitrogen charging conditions, followed by stirring for 12 hours under reflux conditions. After that, the temperature of the mixture was lowered to room temperature, and the thus obtained solid was washed with methylene chloride and methanol, followed by filtering, thereby obtaining clean (E)-5-((6bromobenzo[d][1,3]dioxol-5-yl)methyleneamino)-1H-benzo[d]imidazole-2(3H)-one at 95% yield.

Workup

  1. stirringby stirring for 12 hours under reflux conditions
  2. customwas lowered to room temperature
  3. washthe thus obtained solid was washed with methylene chloride and methanol
  4. filtrationby filtering

Sources & evidence

ORD record
ord-db3d4975092d40f485a262176a88f09f
Source dataset
uspto-grants-2016_04
Patent number
US09321751B2

Reaction notes

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