Formic Acid → HCID 86709237, compound

HRID 2174148Notes

Reaction equation

HRID 2174148 reaction equation
[C:1]1([NH:7][C:8]2[C:9]3[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=3[S:11][C:12]=2[NH2:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:18](O)=O>COC(OC)OC>[C:1]1([N:7]2[C:8]3[C:9]4[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=4[S:11][C:12]=3[N:13]=[CH:18]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 284Formic AcidHCID 86709236HCID 86709236, compound

Product 1

HCID 86709237HCID 86709237, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 9005Trimethyl orthoformateSolvent

Conditions

Temperature
120 °C

Procedure

Into a solution of N3-phenylbenzo[b]thiophene-2,3-diamine (16 g, 66.7 mmol) in trimethoxymethane (200 ml) was added formic acid (1.5 ml, 42.3 mmol) at room temperature. The reaction mixture was subsequently heated at 120° C. for 6 h. After cooling to room temperature, it was quenched with aqueous NaHCO3 solution and extracted with ethyl acetate. Upon evaporation off the solvent, the residue was purified by chromatography on silica gel with hexane/EtOAc (95/5, v/v) as eluent to yield 1-phenyl-1H-benzo[4,5]thieno[2,3-d]imidazole (9.0 g, 54%) as a solid.

Workup

  1. temperatureAfter cooling to room temperature
  2. customit was quenched with aqueous NaHCO3 solution
  3. extractionextracted with ethyl acetate
  4. customUpon evaporation off the solvent
  5. customthe residue was purified by chromatography on silica gel with hexane/EtOAc (95/5

Sources & evidence

ORD record
ord-116b7d2eaf404e4d9f83c14007d44fcb
Source dataset
uspto-grants-2015_06
Patent number
US09059412B2

Reaction notes

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