Phosphorus pentachloride → HCID 19860404, compound

HRID 1721873Notes

Reaction equation

HRID 1721873 reaction equation
[CH3:1][C:2]([NH:5][S:6]([C:9]1[C:10](O)=[N:11][C:12]([S:15][CH3:16])=[N:13][CH:14]=1)(=[O:8])=[O:7])([CH3:4])[CH3:3].P(Cl)(Cl)(Cl)(Cl)[Cl:19]>>[Cl:19][C:10]1[C:9]([S:6]([NH:5][C:2]([CH3:4])([CH3:3])[CH3:1])(=[O:8])=[O:7])=[CH:14][N:13]=[C:12]([S:15][CH3:16])[N:11]=1

Participants

3

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 178503480HCID 178503480, compound

Product 1

HCID 19860404HCID 19860404, compoundYield 71.2%

Procedure

N-(1,1-Dimethylethyl)-4-hydroxy-2-(methylthio)-5-pyrimidinesulfonamide (5.0 g, 18.05 mmol) and finely ground PCl5 (3.95 g, 18.95 mmol, 1.05 eq) were mixed as dry solids. Enough POCl3 was added to make a slurry (7 mL) and the mixture was warmed. The mixture loosened, turned more yellow, evolved a gas, and became homogeneous over a 10 minute period. The reaction was cooled to ambient temperature, diluted with methylene chloride and toluene and evaporated to dryness in vacuo to yield a pale yellow solid. The crude solid was crystallized from ethanol and water to give 3.8 g (12.86 mmoles, 71%) of pure product, m.p. 117°-118° C. as a white solid.

Workup

  1. customas dry solids
  2. additionEnough POCl3 was added
  3. temperaturethe mixture was warmed
  4. additiondiluted with methylene chloride and toluene
  5. customevaporated to dryness in vacuo
  6. customto yield a pale yellow solid
  7. customThe crude solid was crystallized from ethanol and water

Sources & evidence

ORD record
ord-e193d1823d1045fe966413d7e2534cb8
Source dataset
uspto-grants-1989_08
Patent number
US04853389

Reaction notes

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