Ammonia → HCID 20338090, compound

HRID 1395746Notes

Reaction equation

HRID 1395746 reaction equation
[CH:1]1[C:11]2[CH2:10][CH2:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[S:6][C:5]=2[CH:4]=[CH:3][C:2]=1[CH:16]([CH3:20])[C:17](O)=[O:18].C([N:23](CC)CC)C.C(Cl)(=O)OCC.N>C(Cl)(Cl)Cl.O>[CH:1]1[C:11]2[CH2:10][CH2:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[S:6][C:5]=2[CH:4]=[CH:3][C:2]=1[CH:16]([CH3:20])[C:17]([NH2:23])=[O:18]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 12443713HCID 12443713, compound

Product 1

HCID 20338090HCID 20338090, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent2×

Procedure

An amount of 55 mg of 2-(10,11-dihydro dibenzo[b,f]thiepin-2-yl)-propionic acid was dissolved in 0.5 ml of chloroform solution containing 0.02 ml of triethylamine and the resulting mixture was added dropwise with ice-cooling over a period of 5 minutes to 0.5 ml of chloroform solution containing 0.02 ml of ethyl chlorocarbonate. The mixture was stirred for 10 minutes at the same temperature, then at room temperature for 30 minutes after introduction of ammonia gas. After the completion of the reaction, to this was added water and the resulting mixture was extracted with chloroform. The extract was washed with dilute sodium hydroxide solution, then saturated sodium chloride solution, and dried over anhydrous sodium sulfate. The solvent was distilled off to obtain pale brown crystals, which were chromatographed over silica gel, eluted with chloroform, and there were obtained pale yellow crystals. These were recrystallized from benzene-n-hexane to give 26 mg of 2-(10,11-dihydro dibenzo[b,f]thiepin-2-yl)-propionamide as colorless crystals having a melting point of 135°-135.5° C.

Workup

  1. additionthe resulting mixture was added dropwise with ice-
  2. customAfter the completion of the reaction
  3. extractionthe resulting mixture was extracted with chloroform
  4. washThe extract was washed with dilute sodium hydroxide solution
  5. dry with materialsaturated sodium chloride solution, and dried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off
  7. customto obtain pale brown crystals, which
  8. customwere chromatographed over silica gel
  9. washeluted with chloroform
  10. customthere were obtained pale yellow crystals
  11. customThese were recrystallized from benzene-n-hexane

Sources & evidence

ORD record
ord-f24ee9be99744ec9a627f6b22b2faac2
Source dataset
uspto-grants-1980_05
Patent number
US04205170

Reaction notes

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