Dimethylformamide → HCID 22664949, compound

HRID 2120051Notes

Reaction equation

HRID 2120051 reaction equation
P(Cl)(Cl)(Cl)=O.[CH:6]([N:9]([C:11]1[CH:12]=[C:13]([OH:17])[CH:14]=[CH:15][CH:16]=1)[CH3:10])([CH3:8])[CH3:7].CN([CH:21]=[O:22])C>>[CH:6]([N:9]([C:11]1[CH:12]=[C:13]([OH:17])[C:14](=[CH:15][CH:16]=1)[CH:21]=[O:22])[CH3:10])([CH3:8])[CH3:7]

Participants

4

Reactant 3

HCID 6228Dimethylformamide2×HCID 24813Phosphorus oxychlorideHCID 23437615HCID 23437615, compound

Product 1

HCID 22664949HCID 22664949, compound

Conditions

Temperature
90 °C

Procedure

11 g (0.118 mol) of phosphorus oxychloride are cautiously added to 33 ml of dry DMF at −5° C. within a period of 5 minutes, during the course of which the temperature of the reaction solution should not exceed 10° C. Subsequently, a solution of 19.4 g (0.1176 mol) of 3-(N-isopropyl-N-methylamino)phenol in 25 ml of dry DMF is added thereto within a period of 10 minutes, during the course of which the temperature of the reaction solution should not exceed 20° C. When the addition is complete, the reaction solution is heated for 2 hours at 90° C. and then immediately poured onto 150 g of ice. The crude mixture is extracted three times with 100 ml of chloroform. The combined organic phases are concentrated under a high vacuum. The oily residue is purified by column chromatography on silica gel (eluant n-hexane/chloroform 95:5). Yield: 5.8 g (26%), colourless liquid.

Workup

  1. customexceed 10° C
  2. customexceed 20° C
  3. additionWhen the addition
  4. extractionThe crude mixture is extracted three times with 100 ml of chloroform
  5. concentrationThe combined organic phases are concentrated under a high vacuum
  6. customThe oily residue is purified by column chromatography on silica gel (eluant n-hexane/chloroform 95:5)

Sources & evidence

ORD record
ord-ce03955ec6f64a4497913e2e2eb9feee
Source dataset
uspto-grants-2004_02
Patent number
US06689733B1

Reaction notes

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