Dimethylformamide → 4-Methyl-5-phenylthiophene-2-carbaldehyde

HRID 2216726Notes

Reaction equation

HRID 2216726 reaction equation
O=P(Cl)(Cl)Cl.CN([CH:9]=[O:10])C.[CH3:11][C:12]1[CH:16]=[CH:15][S:14][C:13]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C([O-])(=O)C.[Na+]>O>[CH:9]([C:15]1[S:14][C:13]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[C:12]([CH3:11])[CH:16]=1)=[O:10]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 517045Sodium AcetateHCID 104196813-Methyl-2-phenylthiophene

Product 1

HCID 123232534-Methyl-5-phenylthiophene-2-carbaldehyde

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.35 mol (32 mL) of POCl3 was added at 0° C. to a 1.0 mol (77 mL) of DMF (excess of DMF used as solvent). At the end of the addition, the mixture was allowed to warm to room temperature and stirred for 1 h. Then it was cooled again to 0° C. and treated with 3-methyl-2-phenylthiophene (60 g, 0.35 mol). The resulting reaction mixture was allowed to reach room temperature and after 12 h stirring at the same temperature was heated at 80° C. for 2 days. Then it was poured into a mixture of ice and water, added of sodium acetate and extracted with CHCl3 (3×150 mL). The organic phase was separated, washed with water until neutral pH, dried over MgSO4 and evaporated off to dryness. The residue was crystallized. Yield 60.2 g (85%).

Workup

  1. additionAt the end of the addition
  2. temperatureThen it was cooled again to 0° C.
  3. customThe resulting reaction mixture
  4. waitto reach room temperature and after 12 h
  5. stirringstirring at the same temperature
  6. temperaturewas heated at 80° C. for 2 days
  7. extractionextracted with CHCl3 (3×150 mL)
  8. customThe organic phase was separated
  9. washwashed with water until neutral pH
  10. dry with materialdried over MgSO4
  11. customevaporated off to dryness
  12. customThe residue was crystallized

Sources & evidence

ORD record
ord-2da98c53a58d4b589ba5e5ae9614e0fe
Source dataset
uspto-grants-2006_09
Patent number
US07112638B2

Reaction notes

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