Methyl Isocyanate → HCID 67929424, compound

HRID 2050881Notes

Reaction equation

HRID 2050881 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.[CH3:21][N:22]=[C:23]=[O:24]>C(Cl)Cl.C(N(CC)CC)C>[CH3:21][NH:22][C:23]([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:24]

Participants

5

Reactant 2

HCID 12228Methyl IsocyanateHCID 19833914ethyl 5,7-dihydro-6H-dibenz[c,e]azepine-6carboximidate

Product 1

HCID 67929424HCID 67929424, compound

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

2.0 g of ethyl 5,7-dihydro-6H-dibenz[c,e]azepine-6-carboximidate are placed in 10 ml of methylene chloride. After the addition of one drop of triethylamine, 0.41 g of methyl isocyanate in 5 ml of methylene chloride is added dropwise. The mixture is then left to stir at room temperature for 2 days. 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-acetone (4:1) as the eluent, and there is obtained ethyl 5,7-dihydro-N-methylcarbamoyl-6H-dibenz[c,e]azepine-6-carboximidate in 2 isomeric forms: isomer A (eluted first), m.p. 176°-178° C.; isomer B: m.p. 137°-139° C.

Workup

  1. additionis added dropwise
  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-acetone (4:1) as the eluent

Sources & evidence

ORD record
ord-9e6d841766a24e2cb41f890f394545f8
Source dataset
uspto-grants-1991_05
Patent number
US05015640

Reaction notes

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