2-Methoxyethanol → HCID 19833968, compound

HRID 2050815Notes

Reaction equation

HRID 2050815 reaction equation
[Na].[CH:2]1[C:12]2[C:11]3[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=3[CH2:9][N:8]([C:17]#[N:18])[CH2:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH3:19][O:20][CH2:21][CH2:22][OH:23]>>[CH:2]1[C:12]2[C:11]3[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=3[CH2:9][N:8]([C:17](=[NH:18])[O:23][CH2:22][CH2:21][O:20][CH3:19])[CH2:7][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 80192-MethoxyethanolHCID 5360545SodiumHCID 198338865,7-dihydro-6H-dibenz[c,e]azepine-6carbonitrile

Product 1

HCID 19833968HCID 19833968, compound

Conditions

Temperature
80 °C

Procedure

20 ml of 2-methoxyethanol are treated portionwise at 60° C. with 0.23 g of sodium. After 30 minutes, 2.2 g of 5,7-dihydro-6H-dibenz[c,e]azepine-6-carbonitrile are added and the mixture is stirred at 80° C. for 1 hour. Subsequently, the 2-methoxyethanol is distilled off at reduced pressure. The residue is poured on to ice-water and the resulting mixture is extracted twice with methylene chloride. The combined extracts are washed twice with water, dried over anhydrous sodium sulfate and evaporated. The residue is chromatographed on silica gel with ethyl acetate and increasing amounts of ethanol as the eluent, and there is obtained 2-methoxyethyl 5,7-dihydro-6H-dibenz[c,e]azepine-6-carboximidate as a syrup, mass spectrum m/e:M+ 296 (6), 237 (45), 194 (100), 178 (74), 165 (49).

Workup

  1. distillationSubsequently, the 2-methoxyethanol is distilled off at reduced pressure
  2. additionThe residue is poured on to ice-water
  3. extractionthe resulting mixture is extracted twice with methylene chloride
  4. washThe combined extracts are washed twice with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated
  7. customThe residue is chromatographed on silica gel with ethyl acetate
  8. temperatureincreasing amounts of ethanol as the eluent

Sources & evidence

ORD record
ord-8c0a5807180a411e9f80a5de913542cf
Source dataset
uspto-grants-1991_05
Patent number
US05015640

Reaction notes

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