Water → N-[2,4-bis(methylthio)-6-methyl-pyridin-3-yl]-2-chloroacetamide

HRID 1080713Notes

Reaction equation

HRID 1080713 reaction equation
[NH2:1][C:2]1[C:3]([S:11][CH3:12])=[N:4][C:5]([CH3:10])=[CH:6][C:7]=1[S:8][CH3:9].C(N(CC)CC)C.[Cl:20][CH2:21][C:22](Cl)=[O:23].O>O1CCCC1>[CH3:12][S:11][C:3]1[C:2]([NH:1][C:22](=[O:23])[CH2:21][Cl:20])=[C:7]([S:8][CH3:9])[CH:6]=[C:5]([CH3:10])[N:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 99903926-Methyl-2,4-bis-methylsulfanylpyridin-3-ylamine

Product 1

HCID 15452513N-[2,4-bis(methylthio)-6-methyl-pyridin-3-yl]-2-chloroacetamideYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 3-amino-2,4-bis(methylthio)-6-methylpyridine (0.38 g, 1.88 mmol) and triethylamine (0.30 mL, 2.07 mmol) in tetrahydrofuran (8 mL) was cooled to 0° C. and treated with a solution of chloroacetyl chloride (0.18 mL, 2.26 mmol) in tetrahydrofuran (4 mL). After being stirred for 10 hours, the mixture was poured into water (100 mL), and this was extracted with ethyl acetate (2×100 mL). The extracts were combined, dried over anhydrous sodium sulfate, filtered and evaporated. The resulting solid was recrystallized to purity from ether, mp 190°-192° C., to afford N-[2,4-bis(methylthio)-6-methyl-pyridin-3-yl]-2-chloroacetamide (0.39 g, 1.41 mmol, 75%).

Workup

  1. extractionthis was extracted with ethyl acetate (2×100 mL)
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customThe resulting solid was recrystallized to purity from ether, mp 190°-192° C.

Sources & evidence

ORD record
ord-a348651d537642a0b6be0223191d5037
Source dataset
uspto-grants-1996_12
Patent number
US05583147

Reaction notes

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