Dimethylformamide → HCID 19956229, compound

HRID 1779492Notes

Reaction equation

HRID 1779492 reaction equation
[CH3:1][C:2]1[C:9]2[N:8]3[CH:10]=[CH:11][CH:12]=[C:7]3/[C:6](=[N:13]/[O:14][CH2:15][CH2:16]Br)/[C:5]=2[S:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:24]([NH2:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.CN(C)C=O>O>[CH3:1][C:2]1[C:9]2[N:8]3[CH:10]=[CH:11][CH:12]=[C:7]3/[C:6](=[N:13]/[O:14][CH2:15][CH2:16][NH:31][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)/[C:5]=2[S:4][CH:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7504BenzylamineHCID 11430Potassium CarbonateHCID 19956208HCID 19956208, compound

Product 1

HCID 19956229HCID 19956229, compoundYield 64.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Add 1 g (3.2 mmol) of (Z)-3-methyl-8-[(2-bromo-ethoxy)imino]thieno[2,3-d]pyrrolo[1,2-a]pyrrole, 0.53 g (3.8 mmol) of potassium carbonate and 0.51 g (4.8 mmol) of benzylamine in succession to 20 ml of N,N-dimethylformamide. The reaction mixture is heated at reflux for 3 hours then, after cooling, is poured into 100 ml of water and extracted with diethyl ether. The ethereal phase is washed with water, dried over magnesium sulfate, rendered colourless with animal charcoal and then concentrated under reduced pressure to yield 0.7 g of the title product in the form of an oil (base).

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux for 3 hours
  3. temperatureafter cooling
  4. extractionextracted with diethyl ether
  5. washThe ethereal phase is washed with water
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-17d2a8251d644502b9de640660512504
Source dataset
uspto-grants-1997_05
Patent number
US05627203

Reaction notes

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