N,N-Diethylaniline → HCID 19604664, compound

HRID 1604768Notes

Reaction equation

HRID 1604768 reaction equation
O[C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[NH:4][C:5]([S:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[N:6]2.C(N(CC)C1C=CC=CC=1)C.P(Cl)(Cl)([Cl:32])=O>>[Cl:32][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[NH:4][C:5]([S:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[N:6]2

Participants

4

Reactant 3

HCID 7061N,N-DiethylanilineHCID 24813Phosphorus oxychlorideHCID 178518047HCID 178518047, compound

Product 1

HCID 19604664HCID 19604664, compound

Procedure

6-Hydroxy-8-benzylthiopurine (7.33 g) is added to a mixture of phosphorous oxychloride (70 ml) and N,N-diethylaniline (7.5 ml), and the mixture refluxed for 2 hours to give a dark-red product. The mixture is concentrated under vacuum and the resulting syrup poured slowly with stirring onto ice (400 g). The mixture is allowed to stand for 15 min., then made strongly alkaline with cold concentrated KOH. The mixture is triturated thoroughly to dissolve most of the syrup and acidified to pH 1 by the slow addition of cold concentrated HCl, with excess ice still present.

Workup

  1. temperaturethe mixture refluxed for 2 hours
  2. customto give a dark-red product
  3. concentrationThe mixture is concentrated under vacuum
  4. additionthe resulting syrup poured slowly
  5. customThe mixture is triturated thoroughly
  6. dissolutionto dissolve most of the syrup
  7. additionacidified to pH 1 by the slow addition of cold concentrated HCl, with excess ice still present

Sources & evidence

ORD record
ord-08d84a5812624f9bb2096e7969d4dcc8
Source dataset
uspto-grants-1999_11
Patent number
US05994629

Reaction notes

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