Triethylamine → HCID 18688864, compound

HRID 128858Notes

Reaction equation

HRID 128858 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]([O:19][CH3:20])[C:15]([O:17][CH3:18])=[CH:16][C:11]=2[S:10][C:9]=1C(O)=O.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:31])C=CC=CC=1.C([N:43]([CH2:46]C)CC)C.[CH2:48]([C:50]1[CH:56]=[CH:55][CH:54]=[C:53]([CH2:57][CH3:58])[C:51]=1[NH2:52])[CH3:49]>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]([O:19][CH3:20])[C:15]([O:17][CH3:18])=[CH:16][C:11]=2[S:10][C:9]=1[NH:43][C:46]([NH:52][C:51]1[C:53]([CH2:57][CH3:58])=[CH:54][CH:55]=[CH:56][C:50]=1[CH2:48][CH3:49])=[O:31]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 113692,6-DiethylanilineHCID 199401P,P-Diphenylphosphinic azideHCID 18688845HCID 18688845, compound

Product 1

HCID 18688864HCID 18688864, compoundYield 78.3%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

To a stirred mixture of 500 mg of 3-(2-chlorophenyl)-5,6-dimethoxy-1-benzothiophen-2-carboxylic acid and 0.32 cc of diphenylphosphoryl azide in 5 cc of benzene was added dropwise 0.15 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, 0.245 cc of 2,6-diethylaniline was added, followed by refluxing for 2 hours. After cooling, water was added to the reaction mixture and extracted with ethyl acetate. 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=3/7) to obtain 554 mg of compound 102.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 30 minutes
  3. temperatureAfter cooling
  4. temperatureby refluxing for 2 hours
  5. temperatureAfter cooling
  6. extractionextracted with ethyl acetate
  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=3/7)

Sources & evidence

ORD record
ord-099302ffa7644e1fbf08eb1a1a0aabd4
Source dataset
uspto-grants-1995_11
Patent number
US05464863

Reaction notes

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