Dimethylformamide → HCID 16740150, compound

HRID 2216734Notes

Reaction equation

HRID 2216734 reaction equation
O=P(Cl)(Cl)Cl.CN([CH:9]=[O:10])C.[CH3:11][C:12]1[S:13][CH:14]=[CH:15][C:16]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C([O-])(=O)C.[Na+]>O>[CH:9]([C:14]1[S:13][C:12]([CH3:11])=[C:16]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:15]=1)=[O:10]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 517045Sodium AcetateHCID 27753082-methyl-3-phenylthiophene

Product 1

HCID 16740150HCID 16740150, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.166 mol (15 mL) of POCl3 was added at 0° C. to a 0.5 mol (39 mL) of DMF. 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 2-methyl-3-phenylthiophene (29 g, 0.166 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 and added of sodium acetate. The precipitate so obtained was filtered, washed with water and subsequently with hexane. The yellow powder was dried in vacuo.

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. customThe precipitate so obtained
  8. filtrationwas filtered
  9. washwashed with water and subsequently with hexane
  10. customThe yellow powder was dried in vacuo

Sources & evidence

ORD record
ord-ce868d2c4bc74e52b7b2143ca0d32e3b
Source dataset
uspto-grants-2006_09
Patent number
US07112638B2

Reaction notes

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