HCID 22288825, compound → HCID 22288831, compound

HRID 2119577Notes

Reaction equation

HRID 2119577 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([NH:11][C:12]1[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][C:13]=1[C:19]([F:22])([F:21])[F:20])=O>O=P(Cl)(Cl)Cl>[ClH:18].[F:20][C:19]([F:22])([F:21])[C:13]1[CH:14]=[CH:15][CH:16]=[C:17]([Cl:18])[C:12]=1[NH:11][C:9]1[NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[N:8]=1

Participants

3

Reactant 1

HCID 22288825HCID 22288825, compound

Product 1

HCID 22288831HCID 22288831, compound

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

0.8 g of 1-(2-aminophenyl)-3-(6-chloro-2-trifluoromethylphenyl)urea was heated under reflux conditions for 5 hours in 10 ml of POCl3, a clear solution resulting. After distilling off the phosphorus oxychloride under reduced pressure, the oily residue was treated with water, slow crystallization taking place. The crystals were filtered off and chromatographed on silica gel using a mixture of 10 parts of dichloromethane and 1 part of methanol. After distilling off the solvent, the residue was dissolved in EA and rendered strongly acidic using a saturated solution of hydrogen chloride gas in diethyl ether. The crystalline precipitate was filtered off. Colorless to slightly yellowish crystals. M.p.: 255-288° C.

Workup

  1. customa clear solution resulting
  2. distillationAfter distilling off the phosphorus oxychloride under reduced pressure
  3. additionthe oily residue was treated with water, slow crystallization
  4. filtrationThe crystals were filtered off
  5. customchromatographed on silica gel using
  6. additiona mixture of 10 parts of dichloromethane and 1 part of methanol
  7. distillationAfter distilling off the solvent
  8. dissolutionthe residue was dissolved in EA
  9. filtrationThe crystalline precipitate was filtered off

Sources & evidence

ORD record
ord-121105b9c17c4e22bbdd397947f22134
Source dataset
uspto-grants-2004_02
Patent number
US06686384B2

Reaction notes

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