2-Amino-4-methylpyridine → HCID 18348765, compound

HRID 2268016Notes

Reaction equation

HRID 2268016 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][N:3]=1.C(N(CC)CC)C.Cl[C:17](Cl)(Cl)[S:18]Cl.[NH2:22][C:23]1[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=1>ClCCl.O>[CH3:8][C:6]1[CH:5]=[CH:4][N:3]2[C:17](=[N:22][C:23]3[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=3)[S:18][N:1]=[C:2]2[CH:7]=1

Participants

7

Reactant 4

HCID 15332-Amino-4-methylpyridineHCID 17274-AminopyridineHCID 8471Triethylamine2×HCID 11666Trichloromethanesulfenyl chloride

Product 1

HCID 18348765HCID 18348765, compoundYield 17%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Procedure

A solution of 3.2 g (30 mmol) of 2-amino-4-methylpyridine and 4.2 ml of triethylamine in 25 ml of dichloromethane is added dropwise at 0° C. to a solution of 3.3 ml (30 mmol) of trichloromethanesulphenyl chloride in 450 ml of dichloromethane, the mixture is stirred for 10 min and a solution of 2.8 g (30 mmol) of 4-aminopyridine and 12 ml of triethylamine in 100 ml of dichloromethane is added dropwise. After stirring at room temperature for 3 h, the mixture is poured into water and extracted with ethyl acetate, the extract is dried and concentrated, and the residue is chromatographed on silica gel (eluant ethyl acetate/isohexane 1:1). 1.2 g of title compound (17% of theory) of m.p. 144-145° C. are isolated.

Workup

  1. stirringAfter stirring at room temperature for 3 h
  2. extractionextracted with ethyl acetate
  3. customthe extract is dried
  4. concentrationconcentrated
  5. customthe residue is chromatographed on silica gel (eluant ethyl acetate/isohexane 1:1)

Sources & evidence

ORD record
ord-de4427a9f6a94383b01893d57c50e0de
Source dataset
uspto-grants-2001_12
Patent number
US06326378B1

Reaction notes

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