Dimethylformamide → HCID 58700835, compound

HRID 2216732Notes

Reaction equation

HRID 2216732 reaction equation
O=P(Cl)(Cl)[Cl:3].CN([CH:9]=[O:10])C.[C:11]1([CH2:17][C:18](=O)[CH3:19])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C([O-])(=O)C.[Na+]>O>[Cl:3][C:18]([CH3:19])=[C:17]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH:9]=[O:10]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7678PhenylacetoneHCID 24813Phosphorus oxychlorideHCID 517045Sodium Acetate

Product 1

HCID 58700835HCID 58700835, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.375 mol (35 mL) of POCl3 was added at 0° C. to a 0.45 mol (35 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 carefully treated with 0.15 mol (20.1 g) of phenylacetone. The resulting reaction mixture was stirred at the same temperature for 1 h. Then it was poured into a mixture of ice and water, added of sodium acetate and extracted with CHC3 (3×50 mL). The organic phase was separated, washed with water until neutral pH, dried over MgSO4 and carefully evaporated off to dryness. The residue was distilled in vacuo, b.p. 90–110° C./0.21 torr.

Workup

  1. additionAt the end of the addition
  2. temperatureThen it was cooled again to 0° C.
  3. customThe resulting reaction mixture
  4. stirringwas stirred at the same temperature for 1 h
  5. extractionextracted with CHC3 (3×50 mL)
  6. customThe organic phase was separated
  7. washwashed with water until neutral pH
  8. dry with materialdried over MgSO4
  9. customcarefully evaporated off to dryness
  10. distillationThe residue was distilled in vacuo, b.p. 90–110° C./0.21 torr

Sources & evidence

ORD record
ord-d3e54dfd5f5d4fed9a11d2f16b09858c
Source dataset
uspto-grants-2006_09
Patent number
US07112638B2

Reaction notes

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