Aniline → N-[4-(2-Chlorophenyl)-2-phenylpyrimidin-5-yl]-N'-phenylurea

HRID 1440780Notes

Reaction equation

HRID 1440780 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:13](C(O)=O)=[CH:12][N:11]=[C:10]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:9]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:30])C=CC=CC=1.C([N:42]([CH2:45]C)CC)C.[NH2:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1>FC1C=CC=CC=1.O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:13]([NH:42][C:45]([NH:47][C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)=[O:30])=[CH:12][N:11]=[C:10]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:9]=1

Participants

7

Reactant 4

HCID 6115AnilineHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 158187504-(2-Chlorophenyl)-2-phenyl-5-pyrimidinecarboxylic acid

Product 1

HCID 15818751N-[4-(2-Chlorophenyl)-2-phenylpyrimidin-5-yl]-N'-phenylureaYield 49.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 10008FluorobenzeneSolvent

Procedure

To a stirred mixture of 311 mg of 4-(2-chlorophenyl)-2-phenyl-5-pyrimidinecarboxylic acid and 0.26 cc of diphenylphosphoryl azide in 5 cc of fluorobenzene was added dropwise 0.15 cc of triethylamine at room temperature. The resulting mixture was stirred at room temperature for 30 minutes and then heated at a temperature of 65°-70° C. for 10 minutes. After cooling, 0.11 cc of aniline was added and the resulting mixture was stirred heated at a temperature of 70° C. for 2 hours. After cooling, water was added to the reaction mixture and extracted with chloroform. The extract was dried over magnesium sulfate, and distilled to remove the solvent. The crude product thus obtained was purified by a silica gel column chromatography (eluent: chloroform) to obtain 200 mg of compound 7.

Workup

  1. temperatureheated at a temperature of 65°-70° C. for 10 minutes
  2. temperatureAfter cooling
  3. stirringthe resulting mixture was stirred
  4. temperatureheated at a temperature of 70° C. for 2 hours
  5. temperatureAfter cooling
  6. extractionextracted with chloroform
  7. dry with materialThe extract was dried over magnesium sulfate
  8. distillationdistilled
  9. customto remove the solvent
  10. customThe crude product thus obtained
  11. customwas purified by a silica gel column chromatography (eluent: chloroform)

Sources & evidence

ORD record
ord-529c5fe8cfc945baa436a42ab4edefd8
Source dataset
uspto-grants-1996_03
Patent number
US05500424

Reaction notes

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