Ammonia → HCID 20338038, compound

HRID 1395766Notes

Reaction equation

HRID 1395766 reaction equation
[N:1]1[C:11]2[S:10][C:9]3[CH:12]=[C:13]([CH:16]([CH3:20])[C:17](O)=[O:18])[CH:14]=[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.C(Cl)(Cl)Cl.N>C(OCC)(=O)C.C(O)(=O)C>[N:1]1[C:11]2[S:10][C:9]3[CH:12]=[C:13]([CH:16]([CH3:20])[C:17]([NH2:27])=[O:18])[CH:14]=[CH:15][C:8]=3[CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 6212Chloroform2×HCID 10868DicyclohexylcarbodiimideHCID 20338037HCID 20338037, compound

Product 1

HCID 20338038HCID 20338038, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

The mixture of 80 mg of 2-(5,6-dihydro benzo[b]pyrido-[3,2-f]thiepin-9-yl)-propionic acid, 120 mg of dicyclohexylcarbodiimide and 5 ml of chloroform was stirred at 0° C. for 20 minutes under a stream of nitrogen. To this was added dropwise 1 ml of chloroform containing excessive amount of ammonia and the resulting mixture was stirred for 2 hours at 0° C., then at room temperature for 1 hour. To this was added 50 g of ice-water and the mixture was acidified with acetic acid and extracted with chloroform. The extract was washed with water, 5% sodium hydrogencarbonate solution, then water, and dried over anhydrous sodium sulfate. The solvent was distilled off to obtain the residue, which was dissolved in ethyl acetate and filtered. The filtrate was freed of the solvent to obtain the residue, which was chromatographed over silica gel, eluted with chloroform/ethanol(100/1), and there was obtained 63 mg of 2-(5,6-dihydro benzo[b]pyrido[3,2-f]thiepin-9 -yl)-propionamide as colorless glutinous substance.

Workup

  1. stirringthe resulting mixture was stirred for 2 hours at 0° C.
  2. waitat room temperature for 1 hour
  3. extractionextracted with chloroform
  4. washThe extract was washed with water, 5% sodium hydrogencarbonate solution
  5. dry with materialwater, and dried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off
  7. customto obtain the residue, which
  8. filtrationfiltered
  9. customto obtain the residue, which
  10. customwas chromatographed over silica gel
  11. washeluted with chloroform/ethanol(100/1)

Sources & evidence

ORD record
ord-eb27c7686bb74abcb2106e7eb6fa7162
Source dataset
uspto-grants-1980_05
Patent number
US04205170

Reaction notes

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