Sodium Hydroxide → HCID 20338043, compound

HRID 1395759Notes

Reaction equation

HRID 1395759 reaction equation
[C:1]([CH:3]([C:5]1[CH:10]=[CH:9][C:8]([S:11][C:12]2[C:17]([CH2:18][C:19]([OH:21])=O)=[CH:16][CH:15]=[CH:14][N:13]=2)=[CH:7][CH:6]=1)[CH3:4])#[N:2].[OH-:22].[Na+]>>[O:21]=[C:19]1[CH2:18][C:17]2[CH:16]=[CH:15][CH:14]=[N:13][C:12]=2[S:11][C:8]2[CH:9]=[CH:10][C:5]([CH:3]([CH3:4])[C:1]([NH2:2])=[O:22])=[CH:6][C:7]1=2

Participants

3

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 20338072HCID 20338072, compound

Product 1

HCID 20338043HCID 20338043, compound

Conditions

Temperature
150 °C

Procedure

The mixture of 101 mg of 2-[4'-(α-cyanoethyl)-phenylthio]-3-pyridylacetic acid and 2 g of polyphosphoric acid was stirred at 150° C. for 65 minutes. After cooling, to this was added ice-water and the mixture was neutralized with conc. sodium hydroxide solution and 3% sodium hydroxide solution, then was made alkaline therewith. The resulting mixture was extracted with ethyl acetate and the extract was washed with 3% sodium hydroxide solution and dried over anhydrous sodium sulfate. The solvent was distilled off to obtain 36 mg of yellow glutinous substance, which was chromatographed over silica gel, eluted with n-hexane/acetone (2/1) and there was obtained 25 mg of 2-(5,6-dihydro-6-oxo benzo[b]pyrido[3,2-f]-thiepin-8-yl)-propionamide as colorless glutinous substance. This was solidified with ethanol to give crystals having a melting point of 175°-180° C. These were recrystallized from ethanol to give crystals having a melting point of 190°-192.5° C.

Workup

  1. temperatureAfter cooling
  2. extractionThe resulting mixture was extracted with ethyl acetate
  3. washthe extract was washed with 3% sodium hydroxide solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off
  6. customto obtain 36 mg of yellow glutinous substance, which
  7. customwas chromatographed over silica gel
  8. washeluted with n-hexane/acetone (2/1)

Sources & evidence

ORD record
ord-6593aa4bc1dc490784657c57d33a7e53
Source dataset
uspto-grants-1980_05
Patent number
US04205170

Reaction notes

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