Acetic Acid → HCID 20338036, compound

HRID 1395762Notes

Reaction equation

HRID 1395762 reaction equation
[N:1]1[C:11]2[S:10][C:9]3[CH:12]=[CH:13][C:14]([CH:16]([CH3:20])[C:17](O)=[O:18])=[CH:15][C:8]=3[CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.C1([N:27]=C=NC2CCCCC2)CCCCC1.N.C(O)(=O)C>C(Cl)Cl.C(Cl)(Cl)Cl>[N:1]1[C:11]2[S:10][C:9]3[CH:12]=[CH:13][C:14]([CH:16]([CH3:20])[C:17]([NH2:27])=[O:18])=[CH:15][C:8]=3[CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 222AmmoniaHCID 10868DicyclohexylcarbodiimideHCID 20338034HCID 20338034, compound

Product 1

HCID 20338036HCID 20338036, compoundYield 76.3%

Reagents, catalysts & solvents 2

HCID 6212ChloroformCatalystHCID 6344DichloromethaneSolvent2×

Procedure

An amount of 50 mg of 2-(5,6-dihydro benzo[b]pyrido[3,2-f]-thiepin-8-yl)-propionic acid was dissolved in the mixed solvents of 20 ml of methylene chloride and 20 drops of chloroform by heating, and to this were added 50 mg of dicyclohexylcarbodiimide with ice-cooling, then dropwise 3 ml of methylene chloride saturated with liquid ammonia. The resulting mixture was stirred for 1.5 hours under a stream of nitrogen. After the completion of the reaction, to the mixture were added pieces of ice and acetic acid and the resulting mixture was extracted with chloroform. The extract was washed with saturated sodium hydrogencarbonate solution, then saturated sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was distilled off to obtain the residue, which was chromatographed over silica gel, eluted with n-hexane/acetone (4/1-1/1), and there was obtained colorless solid. This was recrystallized from ethyl acetate to give 38 mg of 2-(5,6-dihydro benzo[b]pyrido[3,2-f]-thiepin-8-yl)-propionamide as colorless crystals having a melting point of 173.5°-175° C.

Workup

  1. temperatureby heating
  2. temperaturecooling
  3. customAfter the completion of the reaction
  4. extractionthe resulting mixture was extracted with chloroform
  5. washThe extract was washed with saturated sodium hydrogencarbonate solution
  6. dry with materialsaturated sodium chloride solution and dried over anhydrous sodium sulfate
  7. distillationThe solvent was distilled off
  8. customto obtain the residue, which
  9. customwas chromatographed over silica gel
  10. washeluted with n-hexane/acetone (4/1-1/1)
  11. customthere was obtained colorless solid
  12. customThis was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-80d00903d85744b39c2871e927c0c7a0
Source dataset
uspto-grants-1980_05
Patent number
US04205170

Reaction notes

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