Hydrochloric Acid → HCID 19774691, compound

HRID 654296Notes

Reaction equation

HRID 654296 reaction equation
[O:1]=[C:2]1[CH:7]([C:8](=[O:11])[CH2:9][CH3:10])[C:6](=[O:12])[CH2:5][CH:4]([C:13]#[N:14])[CH2:3]1.[CH3:15][SH:16].[ClH:17]>C(OCC)C>[ClH:17].[O:12]=[C:6]1[CH:7]([C:8](=[O:11])[CH2:9][CH3:10])[C:2](=[O:1])[CH2:3][CH:4]([C:13]([S:16][CH3:15])=[NH:14])[CH2:5]1

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 878MethanethiolHCID 19774688HCID 19774688, compound

Product 1

HCID 19774691HCID 19774691, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

5.0 g (0.026 mol) of 3,5-dioxo-4-propionylcyclohexanecarbonitrile and 1.37 g (0.028 mol) of methyl mercaptan were dissolved in 100 ml of dry diethyl ether. The solution was cooled to 0° C. and then a vigorous stream of dry hydrogen chloride was passed through it. After 0.5 h the gas stream was turned off, and the reaction mixture was slowly warmed to room temperature. It was again cooled to 0° C., hydrogen chloride was passed in (0.5 h) and then the cooling was removed and the mixture was left to stand overnight. The crystals which formed were filtered off with suction and dried in vacuo: 5.4 g (74% of theory) of compound 2.1 [melting point 161° C. (decomposition)].

Workup

  1. temperaturethe reaction mixture was slowly warmed to room temperature
  2. temperatureIt was again cooled to 0° C.
  3. customwas passed in (0.5 h)
  4. customthe cooling was removed
  5. waitthe mixture was left
  6. waitto stand overnight
  7. customThe crystals which formed
  8. filtrationwere filtered off with suction
  9. customdried in vacuo

Sources & evidence

ORD record
ord-1051d6866e8c466792769cafb63410f0
Source dataset
uspto-grants-1992_07
Patent number
US05130453

Reaction notes

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