Formic Acid → HCID 178507425, compound

HRID 628579Notes

Reaction equation

HRID 628579 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 K2CO 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-f40acc6d8331408a92879cb75d5c6f28
Source dataset
uspto-grants-2016_04
Patent number
US09314456B2

Reaction notes

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