6-Methyl-2,4-bis-methylsulfanylpyridin-3-ylamine → HCID 21989745, compound

HRID 2257160Notes

Reaction equation

HRID 2257160 reaction equation
[CH2:1]([S:7][CH:8]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[C:9](Cl)=[O:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[NH2:20][C:21]1[C:22]([S:30][CH3:31])=[N:23][C:24]([CH3:29])=[CH:25][C:26]=1[S:27][CH3:28]>C(Cl)Cl.N1C=CC=CC=1>[CH3:31][S:30][C:22]1[C:21]([NH:20][C:9](=[O:10])[CH:8]([S:7][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])=[C:26]([S:27][CH3:28])[CH:25]=[C:24]([CH3:29])[N:23]=1

Participants

5

Reactant 2

HCID 99903926-Methyl-2,4-bis-methylsulfanylpyridin-3-ylamineHCID 19027841HCID 19027841, compound

Product 1

HCID 21989745HCID 21989745, compoundYield 72.9%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
5 °C

Procedure

A solution of 4.19 g (13.7 mmol) 2-hexylthiodecanoyl chloride, prepared according to Example 4A, in 15 ml methylene chloride was added dropwise with stirring under nitrogen to a solution of 2.75 g (13.7 mmol) 3-amino-2,4-bis(methylthio)-6-methylpyridine in 30 ml pyridine cooled to 5° C. The reaction mixture was stirred at room temperature under nitrogen overnight. Methylene chloride (250 ml) was then added to the reaction mixture and the resulting solution was washed with 3×50 ml 3N aqueous hydrochloric acid solution, 2×50 ml water, 1×50 ml saturated aqueous sodium bicarbonate solution and 1×50 ml brine. The methylene chloride solution was dried over anhydrous sodium sulfate, filtered and concentrated to dryness in vacuo. The solid residue (6.5 g) was recrystallized from petroleum ether to yield 4.7 g of the title compound, m.p. 75°-76.5° C. (72.8% yield).

Workup

  1. additionwas added dropwise
  2. washthe resulting solution was washed with 3×50 ml 3N aqueous hydrochloric acid solution, 2×50 ml water, 1×50 ml saturated aqueous sodium bicarbonate solution and 1×50 ml brine
  3. dry with materialThe methylene chloride solution was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to dryness in vacuo
  6. customThe solid residue (6.5 g) was recrystallized from petroleum ether

Sources & evidence

ORD record
ord-650c6d1cd640405fb92cf7989abf9e92
Source dataset
uspto-grants-1997_08
Patent number
US05656634

Reaction notes

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