Triethylamine → HCID 22902465, compound

HRID 1489774Notes

Reaction equation

HRID 1489774 reaction equation
[CH3:1][C:2]1[CH:20]=[CH:19][C:5]2[O:6][CH2:7][C:8]3[CH:18]=[CH:17][CH:16]=[CH:15][C:9]=3[CH:10]([CH2:11]C(O)=O)[C:4]=2[CH:3]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:28])C=CC=CC=1.C([N:40]([CH2:43]C)CC)C.Cl.[CH:46]([C:49]1[CH:55]=[CH:54][CH:53]=[C:52]([CH:56]([CH3:58])[CH3:57])[C:50]=1[NH2:51])([CH3:48])[CH3:47]>C1(C)C=CC=CC=1.O>[CH:56]([C:52]1[CH:53]=[CH:54][CH:55]=[C:49]([CH:46]([CH3:48])[CH3:47])[C:50]=1[NH:51][C:43]([NH:40][CH2:11][CH:10]1[C:9]2[CH:15]=[CH:16][CH:17]=[CH:18][C:8]=2[CH2:7][O:6][C:5]2[CH:19]=[CH:20][C:2]([CH3:1])=[CH:3][C:4]1=2)=[O:28])([CH3:58])[CH3:57]

Participants

7

Reactant 4

HCID 8471Triethylamine2×HCID 199401P,P-Diphenylphosphinic azideHCID 111834762,6-Di(propan-2-yl)aniline--hydrogen chloride (1/1)HCID 22902461HCID 22902461, compound

Product 1

HCID 22902465HCID 22902465, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

2.0 g of 2-methyl-6,11-dihydrodibenz[b,e]oxepin-11-acetic acid was dissolved in 40 ml of toluene, and 2.52 ml of diphenylphosphoryl azide and 3.12 ml of triethylamine were added thereto at room temperature and stirred for 3.5 hours at the same temperature and then for further one hour at 100° C. The reaction mixture was cooled to room temperature, and 1.92 g of 2,6-diisopropylaniline hydrochloride and 5.0 ml of triethylamine were added thereto and stirred for 30 minutes and then for further 4 hours at 100° C. The reaction mixture was cooled to room temperature, 150 ml of water was added thereto, and the mixture was extracted with ethyl acetate. The thus obtained organic layer was washed first with 1N hydrochloric acid and then with a saturated saline solution in order, and dried and then concentrated to dryness under reduced pressure. The resulting solid residue was purified by silica gel column chromatography (using an eluting solvent of 1/3 (v/v) ethyl acetate/hexane). The crude product was recrystallized from ethyl acetate to obtain 1.16 g of Compound 1.

Workup

  1. waitfor further one hour at 100° C
  2. temperatureThe reaction mixture was cooled to room temperature
  3. stirringstirred for 30 minutes
  4. waitfor further 4 hours at 100° C
  5. temperatureThe reaction mixture was cooled to room temperature
  6. extractionthe mixture was extracted with ethyl acetate
  7. washThe thus obtained organic layer was washed first with 1N hydrochloric acid
  8. customwith a saturated saline solution in order, and dried
  9. concentrationconcentrated to dryness under reduced pressure
  10. customThe resulting solid residue was purified by silica gel column chromatography (
  11. customThe crude product was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-c291736724d84cc08c436741315e33bc
Source dataset
uspto-grants-1997_10
Patent number
US05679703

Reaction notes

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