N,N-Dimethylaniline → HCID 22505949, compound

HRID 2105135Notes

Reaction equation

HRID 2105135 reaction equation
[C:1]1([CH2:7][S:8][C:9]2[NH:18][C:17]3[NH:16][C:15](=[O:19])[CH2:14][S:13][C:12]=3[C:11](=O)[N:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN(C)C1C=CC=CC=1.C(=O)(O)[O-].[Na+].P(Cl)(Cl)([Cl:37])=O>>[Cl:37][C:11]1[C:12]2[S:13][CH2:14][C:15](=[O:19])[NH:16][C:17]=2[N:18]=[C:9]([S:8][CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[N:10]=1

Participants

5

Reactant 4

HCID 949N,N-DimethylanilineHCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 178516922HCID 178516922, compound

Product 1

HCID 22505949HCID 22505949, compound

Procedure

A suspension of the product from step c) (1.5 g), phosphorus oxychloride (10 ml) and N,N-dimethyl aniline (1 ml) was heated under reflux for 2 hours. The mixture was allowed to cool to room temperature and poured carefully into a saturated sodium bicarbonate solution, and stirred for 15 mins. The crude product was extracted into ethyl acetate and purified (SiO2, dichloromethane as eluant) to give the subtitle compound (0.25 g).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. extractionThe crude product was extracted into ethyl acetate
  4. custompurified (SiO2, dichloromethane as eluant)

Sources & evidence

ORD record
ord-63193f6249f845639b88dcab451c5aa0
Source dataset
uspto-grants-2009_08
Patent number
US07579342B2

Reaction notes

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