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

HRID 2399227Notes

Reaction equation

HRID 2399227 reaction equation
Cl[C:2](Cl)(Cl)[S:3]Cl.[NH2:7][C:8]1[CH:13]=[C:12]([CH3:14])[CH:11]=[CH:10][N:9]=1.C(N(CC)CC)C.[NH2:22][C:23]1[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=1>C(Cl)(Cl)Cl.ClCCl.C(OCC)(=O)C.O>[CH3:14][C:12]1[CH:11]=[CH:10][N:9]2[C:2](=[N:22][C:23]3[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=3)[S:3][N:7]=[C:8]2[CH:13]=1

Participants

9

Reactant 4

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

Product 1

HCID 18348765HCID 18348765, compoundYield 17%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3.3 ml (30 mmol) trichloromethanesulphenic acid chloride in 450 ml dichloromethane one adds dropwise at 0° C. a solution of 3.2 g (30 mmol) 2-amino-4-methylpyridine and 4.2 ml triethylamine in 25 ml. dichloromethane, stirs for 10 min and adds dropwise thereto a solution of 2.8 g (30 mmol) 4-aminopyridine and 12 ml triethylamine in 100 ml dichloromethane. After 3 h stirring at room temperature, one pours into water, extracts with ethyl acetate, dries the extract, evaporates and chromatographs on silica gel (elution agent ethyl acetate/isohexane 1:1), One isolates 1,2 g of title compound (17% of theory) of the m.p. 144°-145° C.

Workup

  1. additionadds dropwise
  2. customevaporates

Sources & evidence

ORD record
ord-861fec16abd843c887497a0fbf115067
Source dataset
uspto-grants-1995_09
Patent number
US05447934

Reaction notes

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