2,6-Dimethylaniline → HCID 15285306, compound

HRID 128856Notes

Reaction equation

HRID 128856 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8](C(O)=O)=[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[Cl:19])[C:6]=2[CH:20]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:28])C=CC=CC=1.C([N:40]([CH2:43]C)CC)C.[CH3:45][C:46]1[CH:52]=[CH:51][CH:50]=[C:49]([CH3:53])[C:47]=1[NH2:48]>C1C=CC=CC=1.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([NH:40][C:43]([NH:48][C:47]3[C:49]([CH3:53])=[CH:50][CH:51]=[CH:52][C:46]=3[CH3:45])=[O:28])=[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[Cl:19])[C:6]=2[CH:20]=1

Participants

7

Reactant 4

HCID 68962,6-DimethylanilineHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 15285305HCID 15285305, compound

Product 1

HCID 15285306HCID 15285306, compoundYield 32.2%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

To a stirred mixture of 400 mg of 5-chloro-3-(2-chlorophenyl)-1-benzothiophen-2-carboxylic acid and 0.27 cc of diphenylphosphoryl azide in 3 cc of benzene was added dropwise 0.175 cc of triethylamine at room temperature. The resulting mixture was stirred at room temperature for 15 minutes and then heated under reflux for 20 minutes. After cooling, 0.16 cc of 2,6-dimethylaniline was added and the resulting mixture was stirred at room temperature for 30 minutes, followed by refluxing for 1 hour. After cooling, water was added to the reaction mixture and was 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/hexane=7/3) to obtain 175 mg of compound 64.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 20 minutes
  3. temperatureAfter cooling
  4. stirringthe resulting mixture was stirred at room temperature for 30 minutes
  5. temperatureby refluxing for 1 hour
  6. temperatureAfter cooling
  7. extractionwas extracted with chloroform
  8. dry with materialThe extract was dried over magnesium sulfate
  9. distillationdistilled
  10. customto remove the solvent
  11. customThe crude product thus obtained
  12. customwas purified by a silica gel column chromatography (eluent: chloroform/hexane=7/3)

Sources & evidence

ORD record
ord-d2cdd1f95e4643da91d785679917513e
Source dataset
uspto-grants-1995_11
Patent number
US05464863

Reaction notes

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