Hydrochloric Acid → HCID 70623876, compound

HRID 372236Notes

Reaction equation

HRID 372236 reaction equation
C([C:3]1[CH:16]=[CH:15][C:14]2[S:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6](=[C:17]3[CH2:26][N:25]4[CH:20]([CH2:21][CH2:22][CH2:23][CH2:24]4)[CH2:19][CH2:18]3)[C:5]=2[CH:4]=1)#N.C[Mg]Br.Cl.[CH3:31][CH2:32][O:33]CC>C1C=CC=CC=1>[C:32]([C:3]1[CH:16]=[CH:15][C:14]2[S:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6](=[C:17]3[CH2:26][N:25]4[CH:20]([CH2:21][CH2:22][CH2:23][CH2:24]4)[CH2:19][CH2:18]3)[C:5]=2[CH:4]=1)(=[O:33])[CH3:31]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 70623609HCID 70623609, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 70623876HCID 70623876, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Conditions

Temperature
10 °C

Procedure

A solution of 3.42 g. (0.01 mole) of 3-(2-cyanothioxanthen-9-ylidene)quinolizidine in 50 ml. of benzene is added to a stirred solution of 0.013 mole of methyl magnesium bromide in 5 ml. of ether and 50 ml. of benzene. The stirred mixture is heated at reflux temperature for two hours, then it is cooled to 10° C. and added slowly to 250 ml. of vigorously stirred ice-water. Excess 3 N hydrochloric acid is added to the stirred mixture. The aqueous layer is separated and then it is made alkaline with 2.5 N sodium hydroxide. The mixture is extracted with ethyl acetate. After being dried over magnesium sulfate, the extracts are concentrated. The residue is chromatographed on an alumina column using ether as the eluate. Evaporation of the appropriate fractional eluant gives 3-(2-acetylthioxanthen-9-ylidene)quinolizidine which is converted to a fumarate salt by treatment with a molar equivalent of fumaric acid in methanol.

Workup

  1. temperatureThe stirred mixture is heated
  2. temperatureat reflux temperature for two hours
  3. additionadded slowly to 250 ml
  4. customThe aqueous layer is separated
  5. extractionThe mixture is extracted with ethyl acetate
  6. dry with materialAfter being dried over magnesium sulfate
  7. concentrationthe extracts are concentrated
  8. customThe residue is chromatographed on an alumina column
  9. customEvaporation of the appropriate fractional eluant

Sources & evidence

ORD record
ord-14200f37d7f5432fa67c93868648e22e
Source dataset
uspto-grants-1978_05
Patent number
US04089961

Reaction notes

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