Phosphorus oxychloride → HCID 54175126, compound

HRID 2287226Notes

Reaction equation

HRID 2287226 reaction equation
[C:1]([NH:4][NH:5][C:6]1[CH:11]=[CH:10][N:9]=[C:8]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=2)[N:7]=1)(=O)[CH3:2].P(Cl)(Cl)(Cl)=[O:23].C(=O)(O)[O-].[Na+]>>[F:19][C:18]([F:21])([F:20])[C:14]1[CH:15]=[CH:16][CH:17]=[C:12]([C:8]([NH:9][CH:10]=[CH:11][C:6]2[N:7]=[C:1]([CH3:2])[NH:4][N:5]=2)=[O:23])[CH:13]=1

Participants

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 23459917HCID 23459917, compound

Product 1

HCID 54175126HCID 54175126, compound

Procedure

A mixture of 1-acetyl-2-[2-(3-trifluoromethylphenyl)pyrimidin-4-yl]hydrazine and 15 ml. of phosphorus oxychloride is heated at the reflux temperature for about 20 hours. The cooled reaction mixture is poured over ice, the aqueous mixture neutralized with saturated sodium bicarbonate solution and the product collected. It is then taken up in ether, the ether dried and then evaporated to a solid residue. This residue is triturated with hexane and the precipitate collected. Recrystallization from chloroform/methanol then gives the product of the example, m.p. 153°-154° C.

Workup

  1. customThe cooled reaction mixture
  2. additionis poured over ice
  3. customthe product collected
  4. dry with materialthe ether dried
  5. customevaporated to a solid residue
  6. customThis residue is triturated with hexane
  7. customthe precipitate collected
  8. customRecrystallization from chloroform/methanol
  9. customthen gives the product of the example, m.p. 153°-154° C.

Sources & evidence

ORD record
ord-c7ee6027ad744786b44947c42607d88a
Source dataset
uspto-grants-1981_05
Patent number
US04269980

Reaction notes

Loading…