2,6-Dimethylaniline → HCID 18688887, compound

HRID 128857Notes

Reaction equation

HRID 128857 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]3[CH2:19][CH2:18][CH2:17][C:15]3=[CH:16][C:11]=2[S:10][C:9]=1C(O)=O.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:30])C=CC=CC=1.C([N:42]([CH2:45]C)CC)C.[CH3:47][C:48]1[CH:54]=[CH:53][CH:52]=[C:51]([CH3:55])[C:49]=1[NH2:50]>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]3[CH2:19][CH2:18][CH2:17][C:15]3=[CH:16][C:11]=2[S:10][C:9]=1[NH:42][C:45]([NH:50][C:49]1[C:51]([CH3:55])=[CH:52][CH:53]=[CH:54][C:48]=1[CH3:47])=[O:30]

Participants

7

Reactant 4

HCID 68962,6-DimethylanilineHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 18688837HCID 18688837, compound

Product 1

HCID 18688887HCID 18688887, compoundYield 84.6%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

To a stirred mixture of 400 mg of 3-(2-chlorophenyl)-6,7-dihydro-5H-cyclopenta[f][1]benzothiophene-2-carboxylic acid and 0.27 cc of diphenylphosphoryl azide in 5 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 30 minutes. After cooling, 0.155 cc of 2,6-dimethylaniline was added, followed by refluxing for 2 hours. After cooling, water was added to the reaction mixture and the desired compound 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: ethyl acetate/hexane=15/85) to obtain 454 mg of compound 87.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 30 minutes
  3. temperatureAfter cooling
  4. temperatureby refluxing for 2 hours
  5. temperatureAfter cooling
  6. extractionthe desired compound was extracted 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: ethyl acetate/hexane=15/85)

Sources & evidence

ORD record
ord-082619122ab142ebbbfce1c49c9f8ec0
Source dataset
uspto-grants-1995_11
Patent number
US05464863

Reaction notes

Loading…