Formic Acid → HCID 178507425, compound

HRID 873347Notes

Reaction equation

HRID 873347 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:12][C:11]3[CH:13]=[C:14]([C:17]4[CH:18]=[C:19]([NH2:24])[C:20]([NH2:23])=[CH:21][CH:22]=4)[CH:15]=[CH:16][C:10]=3[N:9]=2)=[CH:4][CH:3]=1.[CH:25](O)=O>O>[NH:9]1[C:10]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][C:20]4[NH:23][CH:25]=[N:24][C:19]=4[CH:18]=3)=[CH:13][C:11]=2[N:12]=[C:8]1[C:5]1[CH:4]=[CH:3][C:2]([NH2:1])=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 284Formic AcidHCID 666790054-(2-(4-Aminophenyl)-1H-benzo[d]imidazol-6-yl)benzene-1,2-diamine

Product 1

HCID 178507425HCID 178507425, compoundYield 6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
160 °C

Procedure

4-(2-(4-Aminophenyl)-1H-benzo[d]imidazol-6-yl)benzene-1,2-diamine (200 mg, 0.64 mmol) and formic acid (0.24 mL, 6.35 mmol) were dissolved in H2O (2 mL) and the mixture heated to 160° C. for 20 min under microwave irradiation. On cooling, a precipitate formed, which was filtered off and washed with water. The filtrate was basified with K2CO3 and stirred for 30 min by which time a precipitate had formed. The mixture was filtered and the precipitate washed with water and dried under suction. The crude product was purified by column chromatography (EtOAc to 85:15 EtOAc-MeOH) to afford the product as a white solid (12 mg, 6%).

Workup

  1. temperatureOn cooling
  2. customa precipitate formed
  3. filtrationwhich was filtered off
  4. washwashed with water
  5. customhad formed
  6. filtrationThe mixture was filtered
  7. washthe precipitate washed with water
  8. customdried under suction
  9. customThe crude product was purified by column chromatography (EtOAc to 85:15 EtOAc-MeOH)

Sources & evidence

ORD record
ord-71efa80c1eeb43c488d834df9be6e127
Source dataset
uspto-grants-2015_03
Patent number
US08975416B2

Reaction notes

Loading…