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

HRID 2396117Notes

Reaction equation

HRID 2396117 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

Part A. 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 thiswas 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%). 1H NMR (CDCl3): δ 7.69 (1H, br s); 6.68 (1H, s); 4.26 (2H, s); 2.53 (3H, s); 2.51 (3H, s); 2.43 (3H, s). Mass spectrum (NH3 -CI/DDIP): m/z 279 (42%); 278 (17%); 277 (100%); 227 (4%).

Workup

  1. extractionthiswas 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-83344fe013a24866beb3649271d5eefb
Source dataset
uspto-grants-1996_02
Patent number
US05491152

Reaction notes

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