Water → HCID 19833896, compound

HRID 2050819Notes

Reaction equation

HRID 2050819 reaction equation
[CH:1]1[C:11]2[C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=3[CH2:8][N:7]([C:16](=[NH:20])[O:17][CH2:18][CH3:19])[CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[C:28](Cl)(=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.O>COC(C)(C)C>[C:28]([N:20]=[C:16]([N:7]1[CH2:6][C:5]2[CH:4]=[CH:3][CH:2]=[CH:1][C:11]=2[C:10]2[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=2[CH2:8]1)[O:17][CH2:18][CH3:19])(=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 19833914ethyl 5,7-dihydro-6H-dibenz[c,e]azepine-6carboximidate

Product 1

HCID 19833896HCID 19833896, compound

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

9.32 g of ethyl 5,7-dihydro-6H-dibenz[c,e]azepine-6-carboximidate are placed in 100 ml of tert.butyl methyl ether with 3.54 g of triethylamine. 4.92 g of benzoyl chloride are added dropwise within about 30 minutes while cooling with an ice bath. The mixture is then left to stir at 0°-5° C. for 20 minutes. The reaction mixture is poured into water and extracted twice with ethyl acetate. The extracts are washed with water and saturated sodium chloride solution, dried over anhydrous sodium sulfate and evaporated. The crude product is dissolved in ethyl acetate while warming and suction filtered over an about 3 cm deep layer of silica gel. The crystals obtained after evaporation of the filtrate are recrystallized from ethanol, and there is obtained ethyl N-benzoyl-5,7-dihydro-6H-dibenz[c,e]azepine-6-carboximidate, m.p. 116°-117° C.

Workup

  1. temperaturewhile cooling with an ice bath
  2. waitThe mixture is then left
  3. extractionextracted twice with ethyl acetate
  4. washThe extracts are washed with water and saturated sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated
  7. dissolutionThe crude product is dissolved in ethyl acetate
  8. temperaturewhile warming
  9. filtrationsuction filtered over an about 3 cm deep layer of silica gel
  10. customThe crystals obtained
  11. customafter evaporation of the filtrate
  12. customare recrystallized from ethanol

Sources & evidence

ORD record
ord-8fb15fbbffcf4df89405b7b5bb68bd2b
Source dataset
uspto-grants-1991_05
Patent number
US05015640

Reaction notes

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