Methyl chloroformate → HCID 54375274, compound

HRID 2050872Notes

Reaction equation

HRID 2050872 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.Cl[C:29]([O:31][CH3:32])=[O:30]>C(Cl)Cl>[CH3:32][O:31][C:29]([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:30]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 19833914ethyl 5,7-dihydro-6H-dibenz[c,e]azepine-6carboximidate

Product 1

HCID 54375274HCID 54375274, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.66 g of ethyl 5,7-dihydro-6H-dibenz[c,e]azepine-6-carboximidate are placed in 15 ml of methylene chloride with 1 g of triethylamine. 0.95 g of methyl chloroformate is added dropwise while cooling with an ice bath. The mixture is then left to stir at room temperature for 2 hours. The reaction mixture is poured on to ice-water and extracted twice with methylene chloride. The extracts are washed with water, dried over anhydrous sodium sulfate and evaporated under reduced pressure. The oily residue is chromatographed on silica gel with n-hexane-ethyl acetate (1:1) as the eluent, and there is obtained ethyl N-methoxycarbonyl-5,7-dihydro-6H-dibenz[c,e]azepine-6-carboximidate as an oil, mass spectrum m/e: M+ 324 (6), 295 (20), 263 (70), 194 (100), 178 (35), 165 (49).

Workup

  1. temperaturewhile cooling with an ice bath
  2. waitThe mixture is then left
  3. extractionextracted twice with methylene chloride
  4. washThe extracts are washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated under reduced pressure
  7. customThe oily residue is chromatographed on silica gel with n-hexane-ethyl acetate (1:1) as the eluent

Sources & evidence

ORD record
ord-415f273e3e564e8e9bcc4d2e36ddbddd
Source dataset
uspto-grants-1991_05
Patent number
US05015640

Reaction notes

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