2,6-Dimethylaniline → HCID 18688835, compound

HRID 128854Notes

Reaction equation

HRID 128854 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:12]2[CH:13]=[C:14]([CH3:18])[C:15]([CH3:17])=[CH:16][C:11]=2[O:10][C:9]=1C(O)=O.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:29])C=CC=CC=1.C([N:41]([CH2:44]C)CC)C.[CH3:46][C:47]1[CH:53]=[CH:52][CH:51]=[C:50]([CH3:54])[C:48]=1[NH2:49]>C1C=CC=CC=1.O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:12]2[CH:13]=[C:14]([CH3:18])[C:15]([CH3:17])=[CH:16][C:11]=2[O:10][C:9]=1[NH:41][C:44]([NH:49][C:48]1[C:50]([CH3:54])=[CH:51][CH:52]=[CH:53][C:47]=1[CH3:46])=[O:29]

Participants

7

Reactant 4

HCID 68962,6-DimethylanilineHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 18688841HCID 18688841, compound

Product 1

HCID 18688835HCID 18688835, compoundYield 66.6%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

To a stirred mixture of 301 mg of 3-(2-chlorophenyl)-5,6-dimethylbenzofuran-2-carboxylic acid and 0.26 cc of diphenylphosphoryl azide in 5 cc of benzene was added dropwise 0.14 cc of triethylamine at room temperature. The resulting mixture was stirred at room temperature for 15 minutes and then heated under reflux for 15 minutes. After cooling, 0.14 cc of 2,6-dimethylaniline was added, followed by refluxing 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 279 mg of compound 36.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 15 minutes
  3. temperatureAfter cooling
  4. temperatureby refluxing 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-b4295ccff6ed455dbec341fabca16645
Source dataset
uspto-grants-1995_11
Patent number
US05464863

Reaction notes

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