Dimethylformamide → HCID 22664951, compound

HRID 2120050Notes

Reaction equation

HRID 2120050 reaction equation
P(Cl)(Cl)(Cl)=O.[CH2:6]([N:8]([C:10]1[CH:11]=[C:12]([OH:16])[CH:13]=[CH:14][CH:15]=1)[CH3:9])[CH3:7].CN([CH:20]=[O:21])C>>[CH2:6]([N:8]([C:10]1[CH:11]=[C:12]([OH:16])[C:13](=[CH:14][CH:15]=1)[CH:20]=[O:21])[CH3:9])[CH3:7]

Participants

4

Reactant 3

HCID 6228Dimethylformamide2×HCID 24813Phosphorus oxychlorideHCID 136091833-[Ethyl(methyl)amino]phenol

Product 1

HCID 22664951HCID 22664951, compound

Conditions

Temperature
90 °C

Procedure

6.14 g (0.066 mol) of phosphorus oxychloride are cautiously added to 19 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 9.9 g (0.066 mol) of 3-(N-ethyl-N-methylamino)phenol in 14 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 100 g of ice. The crude mixture is stirred for 30 minutes. The reaction solution is extracted three times with 100 ml of chloroform. The combined organic phases are concentrated under a high vacuum. The oily residue which remains is purified by column chromatography on silica gel (eluant n-hexanelchloroform 95:5). Yield: 5.8 g (26%), colourless solid.

Workup

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

Sources & evidence

ORD record
ord-57f42a23f2fd4ec09da11dcae5cd938a
Source dataset
uspto-grants-2004_02
Patent number
US06689733B1

Reaction notes

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