Hydrochloric Acid → HCID 20504108, compound

HRID 1702122Notes

Reaction equation

HRID 1702122 reaction equation
[Br:1][C:2]1[CH:17]=[CH:16][C:5]([NH:6][C:7]([CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][C:10]2=[O:15])=[S:8])=[C:4]([F:18])[CH:3]=1.[C-]#N.[K+].Cl.[CH2:23]([OH:25])C>O>[Br:1][C:2]1[CH:17]=[CH:16][C:5]([N:6]2[C:23](=[O:25])[C:10]3([OH:15])[CH:9]([CH2:14][CH2:13][CH2:12][CH2:11]3)[C:7]2=[S:8])=[C:4]([F:18])[CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 702EthanolHCID 9032Potassium CyanideHCID 12832958HCID 12832958, compound

Product 1

HCID 20504108HCID 20504108, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

In 350 ml of ethanol was dissolved 33.0 g of 4'-bromo-2'-fluoro-2-oxocyclohexane-1-thiocarboxanilide, and a solution of 7.0 g of potassium cyanide in 35 ml of water was added to the solution with stirring at room temperature over a 10-minute period, followed by adding 9.2 ml of concentrated hydrochloric acid at 10° to 20° C. over a 1 hour period, while cooling. After stirring was continued at room temperature for 1 hour, 30 ml of concentrated hydrochloric acid and 30 ml of water were added to the reaction mixture, and the mixture was warmed and stirred at 50° to 60° C. for 10 minutes. Upon cooling, there resulted crystals, which were collected by filtration, washed with dilute ethanol and dried, thereby producing 24.5 g (yield of 68%) of the subject compound. Recrystallization from ethanol yielded slightly yellow crystals, m.p. 163°-164° C.

Workup

  1. temperaturewhile cooling
  2. stirringAfter stirring
  3. temperaturethe mixture was warmed
  4. stirringstirred at 50° to 60° C. for 10 minutes
  5. temperatureUpon cooling
  6. customthere resulted crystals, which
  7. filtrationwere collected by filtration
  8. washwashed with dilute ethanol
  9. customdried

Sources & evidence

ORD record
ord-eb049a6ad0a346fe9f20e09ca2952d77
Source dataset
uspto-grants-1983_04
Patent number
US04380466

Reaction notes

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