Acetic Acid → HCID 13134785, compound

HRID 355111Notes

Reaction equation

HRID 355111 reaction equation
[N:1]1[C:11]2[S:10][C:9]3[CH:12]=[CH:13][C:14]([CH2:16][C:17]([OH:19])=O)=[CH:15][C:8]=3[CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.C1([N:26]=C=NC2CCCCC2)CCCCC1.C(Cl)(Cl)Cl.C(O)(=O)C>C(OCC)(=O)C>[N:1]1[C:11]2[S:10][C:9]3[CH:12]=[CH:13][C:14]([CH2:16][C:17]([NH2:26])=[O:19])=[CH:15][C:8]=3[CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6212Chloroform2×HCID 10868DicyclohexylcarbodiimideHCID 13134784HCID 13134784, compound

Product 1

HCID 13134785HCID 13134785, compoundYield 24.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 100 mg of (5,6-dihydro benzo[b]pyrido[3,2-f]-thiepin-8-yl)-acetic acid, 100 mg of dicyclohexylcarbodiimide and 20 ml of chloroform was stirred under a nitrogen atmosphere at 0° C. for 20 minutes. To the resulting mixture was slowly added 1 ml of chloroform containing excess ammonia. The mixture was stirred at 0° C. for 30 minutes and then at room temperature for 1 hour. To this was added 500 g of ice water, and the mixture was acidified with acetic acid and extracted with 50 ml of chloroform. The extract was washed with water, a 5% sodium hydrogen carbonate solution and then with water and dried over anhydrous sodium sulfate. The solvent was distilled off to obtain a residue, to which was added ethyl acetate, and the mixture was filtrated to remove any unsoluble substance. Thereafter, the solvent was removed by distillation to obtain a residue, which was chromatographed over silica gel and eluted with chloroform/ethanol (100/1) to obtain a solid. This was recrystallized from benzene/n-hexane to give 24 mg (yield: 24%) of (5,6-dihydro benzo[b]pyrido[3,2-f]thiepin-8-yl)-acetamide as a colorless powder having a melting point of 165°-166° C.

Workup

  1. stirringThe mixture was stirred at 0° C. for 30 minutes
  2. waitat room temperature for 1 hour
  3. extractionextracted with 50 ml of chloroform
  4. washThe extract was washed with water
  5. dry with materiala 5% sodium hydrogen carbonate solution and then with water and dried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off
  7. customto obtain a residue
  8. filtrationthe mixture was filtrated
  9. customto remove any unsoluble substance
  10. customThereafter, the solvent was removed by distillation
  11. customto obtain a residue, which
  12. customwas chromatographed over silica gel
  13. washeluted with chloroform/ethanol (100/1)
  14. customto obtain a solid
  15. customThis was recrystallized from benzene/n-hexane

Sources & evidence

ORD record
ord-722f93912f2f462db9ec635f76aca59f
Source dataset
uspto-grants-1983_03
Patent number
US04377702

Reaction notes

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