Hydrochloric Acid → HCID 9824264, compound

HRID 1080701Notes

Reaction equation

HRID 1080701 reaction equation
[CH2:1]([S:7][CH:8]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:9]([O-:11])=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[NH2:18][C:19]1[C:20]([S:28][CH3:29])=[N:21][C:22]([CH3:27])=[CH:23][C:24]=1[S:25][CH3:26].C[Al](C)C.Cl>C(Cl)Cl.C1(C)C=CC=CC=1>[CH3:29][S:28][C:20]1[C:19]([NH:18][C:9](=[O:11])[CH:8]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[S:7][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])=[C:24]([S:25][CH3:26])[CH:23]=[C:22]([CH3:27])[N:21]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 99903926-Methyl-2,4-bis-methylsulfanylpyridin-3-ylamineHCID 16682925TrimethylaluminumHCID 23365775HCID 23365775, compound

Product 1

HCID 9824264HCID 9824264, compoundYield 7.6%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution α-hexylthio-phenylacetate (204 mg) and 3-amino-2,4-bis(methylthio)-6-methyl-pyridine (146 mg) in methylene chloride (5 ml) was added dropwise 2M solution of trimethylaluminum in toluene (0.4 ml), and the mixture was refluxed for 16 hours. After cooling to 0° it was acidified slowly with 1N hydrochloric acid, and extracted with ethyl acetate twice. The combined extracts were washed with water and brine, dried (magnesium sulfate) and evaporated to give a solid residue. It was purified by a column chromatography on silica gel with elution by 2:8 ethyl acetate-hexane to give a solid residue. Crystallization from ethyl ether and hexane to provide pure N-[2,4-bis(methylthio)-6-methyl-3-pyridyl]-α-hexylthio-phenylacetamide (24 mg).

Workup

  1. temperaturethe mixture was refluxed for 16 hours
  2. temperatureAfter cooling to 0° it
  3. extractionextracted with ethyl acetate twice
  4. washThe combined extracts were washed with water and brine
  5. dry with materialdried (magnesium sulfate)
  6. customevaporated
  7. customto give a solid residue
  8. customIt was purified by a column chromatography on silica gel with elution by 2:8 ethyl acetate-hexane
  9. customto give a solid residue
  10. customCrystallization from ethyl ether and hexane

Sources & evidence

ORD record
ord-51c8e065681a4e2c9f18d591929a6150
Source dataset
uspto-grants-1996_12
Patent number
US05583147

Reaction notes

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