Acetic Acid → HCID 178518643, compound

HRID 631943Notes

Reaction equation

HRID 631943 reaction equation
[Br:1][C:2]1C=C[C:5]2OCO[C:4]=2[C:3]=1C=O.[CH3:13][CH:14]([OH:16])[CH3:15].[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:28](O)(=[O:30])C>>[Br:1][C:2]1[CH:3]=[C:4](/[CH:5]=[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)[C:13]2[O:30][CH2:28][O:16][C:14]=2[CH:15]=1

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 3776IsopropanolHCID 667655-Amino-2-hydroxybenzimidazoleHCID 110316405-Bromo-1,3-benzodioxole-4-carboxaldehyde

Product 1

HCID 178518643HCID 178518643, compoundYield 80%

Procedure

5-bromobenzo[d][1,3]dioxol-4-carbaldehyde (0.25 g, 1.09 mmol), IPA (5 ml), and 5-amino-1H-benzo[d]imidazole-2(3H)-one (0.16 g, 1.09 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-4-yl)methyleneamino)-1H-benzo[d]imidazole-2(3H)-one at 80% 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-e7010626c6924074a7fa631410c7854e
Source dataset
uspto-grants-2016_04
Patent number
US09321751B2

Reaction notes

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