N,N-Dimethylaniline → HCID 178478351, compound

HRID 1289528Notes

Reaction equation

HRID 1289528 reaction equation
P(Cl)(Cl)([Cl:3])=O.CN(C)C1C=CC=CC=1.O[C:16]1[NH:21][C:20]2=[CH:22][CH:23]=[CH:24][C:19]2=C(O)[N:17]=1.Cl[CH2:27][Cl:28]>>[Cl:3][C:16]1[NH:21][C:20]2=[CH:22][CH:23]=[CH:24][C:19]2=[C:27]([Cl:28])[N:17]=1

Participants

5

Reactant 4

HCID 949N,N-DimethylanilineHCID 6344DichloromethaneHCID 24813Phosphorus oxychlorideHCID 178518296HCID 178518296, compound

Product 1

HCID 178478351HCID 178478351, compoundYield 15%

Procedure

A mixture solution of phosphorous oxychloride(49 ml), N,N-dimethylaniline(8.0 ml) and 2,4-dihydroxycyclopenta[d]pyrimidine(15.4 g, 0.1 mol) prepared in the above Step 2 was heated to reflux for 3 hours and cooled to a room temperature. After the reaction mixture was diluted with dichloromethane, the diluted solution was added to ice water, while maintaining the temperature of the reaction system below 10° C. The reaction mixture was extracted with dichloromethane, dried over anhydrous sodium sulfate and concentrated in vacuo to give 2.8 g of titled compound as an oily form. (Yield: 15%)

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 3 hours
  3. temperaturewhile maintaining the temperature of the reaction system below 10° C
  4. extractionThe reaction mixture was extracted with dichloromethane
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9a95b474901e4554a0fad4f76d83c963
Source dataset
uspto-grants-1998_05
Patent number
US05750531

Reaction notes

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