HCID 19940140, compound → HCID 57183713, compound

HRID 476828Notes

Reaction equation

HRID 476828 reaction equation
[C:1]([C:3]1[CH:7]=[C:6](C2SC=CC=2)[NH:5][C:4]=1[C:13]1[S:14][CH:15]=[CH:16][CH:17]=1)#[N:2]>C1COCC1>[C:1]([C:3]1[C:7]([C:13]2[S:14][CH:15]=[CH:16][CH:17]=2)=[CH:6][NH:5][C:4]=1[C:13]1[S:14][CH:15]=[CH:16][CH:17]=1)#[N:2]

Participants

3

Reactant 1

HCID 19940140HCID 19940140, compound

Product 1

HCID 57183713HCID 57183713, compoundYield 106.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 0.8 g (3 mmol) of 3-cyano-2,5-dithienylpyrrole (XVII) in 20 mL of dry THF was added 8 mL of a 1M solution of borane-tetrahydrofuran complex in THF. After the initial exothermic reaction subsided, the mixture was heated to reflux under an inert (argon gas) atmosphere overnight. The solvents then were evaporated in vacuo and the residue partitioned between CHCl3 and a 3N hydrochloric acid (HCl) solution. The CHCl3 layer then was extracted three times with 10 mL portions of 3N HCl dried over sodium sulfate, filtered, and concentrated in vacuo to give 410 mg of unreacted 3-cyanodithienylpyrrole (XVII).

Workup

  1. customAfter the initial exothermic reaction
  2. temperaturethe mixture was heated
  3. temperatureto reflux under an inert (argon gas) atmosphere overnight
  4. customThe solvents then were evaporated in vacuo
  5. customthe residue partitioned between CHCl3
  6. extractionThe CHCl3 layer then was extracted three times with 10 mL portions of 3N HCl
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3c5459a8593b4785b6f96ec99109860d
Source dataset
uspto-grants-1989_12
Patent number
US04886625

Reaction notes

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