Hydrochloric Acid → HCID 86732855, compound

HRID 1579152Notes

Reaction equation

HRID 1579152 reaction equation
[CH2:1]([S:3][C:4]1[CH:26]=[CH:25][C:7]2[N:8]([CH3:24])[C:9]3[CH:23]=[CH:22][CH:21]=[CH:20][C:10]=3[CH2:11][C:12](O)([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:6]=2[CH:5]=1)[CH3:2].Cl>C(O)C>[CH2:1]([S:3][C:4]1[CH:26]=[CH:25][C:7]2[N:8]([CH3:24])[C:9]3[CH:23]=[CH:22][CH:21]=[CH:20][C:10]=3[CH2:11][C:12](=[CH:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:6]=2[CH:5]=1)[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86732856HCID 86732856, compound

Product 1

HCID 86732855HCID 86732855, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 35 g of 2-ethylthio-5-methyl-11-hydroxy-11-ethoxycarbonylmethyl-10,11-dihydro [5H] dibenzo (b,f) azepine, 500 ml of ethanol and 50 ml of 2N hydrochloric acid was stirred for 3 hours at room temperature. The mixture was poured into 2 kg of ice and the mixture was extracted with ethyl acetate. The organic extracts were washed with water, dried over magnesium sulfate and distilled to dryness under reduced pressure. The residue was chromatographed over silica gel with a 98-2 mixture of benzene-ethyl acetate as eluant which was evaporated to obtain 27.3 g of 2-ethylthio-5-methyl-11-ethoxycarbonylmethylene-10,11-dihydro [5H] dibenzo (b,f) azepine in the form of a yellow oil soluble in alcohol, chlorinated solvents and ethyl acetate and insoluble in water.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic extracts were washed with water
  3. dry with materialdried over magnesium sulfate
  4. distillationdistilled to dryness under reduced pressure
  5. customThe residue was chromatographed over silica gel with a 98-2 mixture of benzene-ethyl acetate as eluant which
  6. customwas evaporated

Sources & evidence

ORD record
ord-a600e4a01fc6471392cb56fa5c0d91e8
Source dataset
uspto-grants-1976_01
Patent number
US03931151

Reaction notes

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