Hydrochloric Acid → HCID 12813984, compound

HRID 1579153Notes

Reaction equation

HRID 1579153 reaction equation
[CH2:1]([S:3][C:4]1[CH:25]=[CH:24][C:7]2[N:8]([CH3:23])[C:9]3[CH:22]=[CH:21][CH:20]=[CH:19][C:10]=3[CH2:11][C:12](=[CH:13][C:14]([O:16]CC)=[O:15])[C:6]=2[CH:5]=1)[CH3:2].[OH-].[K+].Cl>C(O)C>[CH2:1]([S:3][C:4]1[CH:25]=[CH:24][C:7]2[N:8]([CH3:23])[C:9]3[CH:22]=[CH:21][CH:20]=[CH:19][C:10]=3[CH:11]=[C:12]([CH2:13][C:14]([OH:16])=[O:15])[C:6]=2[CH:5]=1)[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 86732855HCID 86732855, compound

Product 1

HCID 12813984HCID 12813984, compoundYield 78.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 27.3 g of 2-ethylthio-5-methyl-11-ethoxycarbonylmethylene-10,11-dihydro [5H] dibenzo (b,f) azepine in 750 ml of ethanol was stirred until complete dissolution occured and then 120 g of potassium hydroxide were added. The mixture was held at room temperature for 30 minutes and then was poured into a mixture of 2 kg of ice and 270 ml of hydrochloric acid. The mixture was stirred for 30 minutes and was extracted with methylene chloride. The organic phase was washed with water, dried over magnesium sulfate and distilled to dryness under reduced pressure. The 23 g of product were dissolved in 200 ml of refluxing ethyl acetate and the solution was filtered and was slightly concentrated. Crystallization was induced and the mixture was iced for 30 minutes and then vacuum filtered. The recovered precipitate was washed with ethyl acetate and dried under reduced pressure to obtain 19.64 g of 2-ethylthio-5-methyl-11 -carboxymethyl [5H] dibenzo (b,f) azepine which was used as is for the next step. For analysis, the product was crystallized from ethyl acetate and was a yellow crystalline solid melting at 164°C.

Workup

  1. stirringThe mixture was stirred for 30 minutes
  2. extractionwas extracted with methylene chloride
  3. washThe organic phase was washed with water
  4. dry with materialdried over magnesium sulfate
  5. distillationdistilled to dryness under reduced pressure
  6. dissolutionThe 23 g of product were dissolved in 200 ml of refluxing ethyl acetate
  7. filtrationthe solution was filtered
  8. concentrationwas slightly concentrated
  9. customCrystallization
  10. waitthe mixture was iced for 30 minutes
  11. filtrationvacuum filtered
  12. washThe recovered precipitate was washed with ethyl acetate
  13. customdried under reduced pressure

Sources & evidence

ORD record
ord-0f1fad8c40474b059047bab1ee55dd95
Source dataset
uspto-grants-1976_01
Patent number
US03931151

Reaction notes

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