Dimethylformamide → HCID 21943913, compound

HRID 2216730Notes

Reaction equation

HRID 2216730 reaction equation
O=P(Cl)(Cl)Cl.[C:6]1([C:12]2[S:13][CH:14]=[CH:15][C:16]=2[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.CN([CH:26]=[O:27])C.[OH-].[Na+]>O>[CH:26]([C:14]1[S:13][C:12]([C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=2)=[C:16]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:15]=1)=[O:27]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 28017362,3-diphenylthiophene

Product 1

HCID 21943913HCID 21943913, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

POCl3 (80 mmol, 7.32 mL) was added at 0° C. to a solution of 2,3-diphenylthiophene (18 g, 76 mmol) in DMF (18 mL, 0.23 mol). At the end of the addition, the reaction mixture was allowed to warm to room temperature and refluxed for 3 h. Then it was cooled to room temperature and poured into a mixture of ice and a 10% solution of sodium hydroxide in water. The oily precipitate obtained was filtered and washed with cold methanol and hexane. The residue was crystallized. Yield 15 g (75%).

Workup

  1. additionAt the end of the addition
  2. temperaturerefluxed for 3 h
  3. temperatureThen it was cooled to room temperature
  4. additionpoured into a mixture of ice
  5. customThe oily precipitate obtained
  6. filtrationwas filtered
  7. washwashed with cold methanol and hexane
  8. customThe residue was crystallized

Sources & evidence

ORD record
ord-d1f5b60b49774efab905a0ca66d062cf
Source dataset
uspto-grants-2006_09
Patent number
US07112638B2

Reaction notes

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