HCID 69522581, compound → HCID 178478965, compound

HRID 349388Notes

Reaction equation

HRID 349388 reaction equation
[NH2:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]1[NH:8][C:9]([NH:11][C:12]1[C:17]([C:18]([F:21])([F:20])[F:19])=[CH:16][CH:15]=[CH:14][C:13]=1[Cl:22])=O>P(Cl)(Cl)(Cl)=O>[ClH:22].[Cl:22][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]([C:18]([F:21])([F:20])[F:19])[C:12]=1[N:11]=[C:9]1[NH:8][C@@H:3]2[CH2:4][CH2:5][CH2:6][CH2:7][C@H:2]2[NH:1]1

Participants

3

Reactant 1

HCID 69522581HCID 69522581, compound

Product 1

HCID 178478965HCID 178478965, compoundYield 133%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

0.57 g of N-(trans-2-aminocyclohexyl)-N′-(2-chloro-6-trifluoromethylphenyl)urea in 20 ml of phosphorus oxychloride (POCl3) was boiled at reflux for 4–5 hours. The POCl3 was distilled off, water was added to the residue and the pH was adjusted to 7–8 using 2N NaOH. The mixture was then extracted with ethyl acetate, the organic solvent was distilled off and the residue was chromatographed on silica gel using a mixture of 20 parts of ethyl acetate, 10 parts of n-heptane and 3 parts of glacial acetic acid. After removal of the eluent by distillation, the white solid residue was dissolved in a little ethyl acetate and acidified using a saturated solution of HCl gas in diethyl ether. Removal of the solvent by distillation and treatment of the residue with diisopropyl ether gave 0.4 g of the desired product as a solid of m.p. 160–165° C.

Workup

  1. temperatureat reflux for 4–5 hours
  2. distillationThe POCl3 was distilled off
  3. additionwater was added to the residue
  4. extractionThe mixture was then extracted with ethyl acetate
  5. distillationthe organic solvent was distilled off
  6. customthe residue was chromatographed on silica gel using
  7. additiona mixture of 20 parts of ethyl acetate, 10 parts of n-heptane and 3 parts of glacial acetic acid
  8. customAfter removal of the eluent
  9. distillationby distillation
  10. dissolutionthe white solid residue was dissolved in a little ethyl acetate
  11. customRemoval of the solvent
  12. distillationby distillation and treatment of the residue with diisopropyl ether

Sources & evidence

ORD record
ord-f5cfe90444b742f69bb4df8ef420c73a
Source dataset
uspto-grants-2007_02
Patent number
US07179829B2

Reaction notes

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