4-(Chloromethyl)-2-methyl-1,3-thiazole → (2-Methyl-4-thiazolyl)methyl 2-cyanonicotinate

HRID 1165163Notes

Reaction equation

HRID 1165163 reaction equation
[C:1]([C:3]1[N:11]=[CH:10][CH:9]=[CH:8][C:4]=1[C:5]([O-:7])=[O:6])#[N:2].[K+].Cl[CH2:14][C:15]1[N:16]=[C:17]([CH3:20])[S:18][CH:19]=1>C(#N)C.C1OCCOCCOCCOCCOCCOC1>[C:1]([C:3]1[N:11]=[CH:10][CH:9]=[CH:8][C:4]=1[C:5]([O:7][CH2:14][C:15]1[N:16]=[C:17]([CH3:20])[S:18][CH:19]=1)=[O:6])#[N:2]

Participants

5

Reactant 2

HCID 7363414-(Chloromethyl)-2-methyl-1,3-thiazoleHCID 23690323Potassium 2-cyanonicotinate

Product 1

HCID 14330271(2-Methyl-4-thiazolyl)methyl 2-cyanonicotinateYield 41%

Reagents, catalysts & solvents 2

HCID 2855718-Crown-6CatalystHCID 6342AcetonitrileSolvent

Procedure

A mixture of potassium 2-cyanonicotinate (4.1 g; 0.022 mole), 4-chloromethyl-2-methylthiazole (2.95 g; 0.02 mole) and 18-crown-6-ether (0.13 g; 0.0005 mole) in acetonitrile (50 cc) is brought to reflux for 8 hours. The solvent is then evaporated off and the residue taken up in water and extracted with dichloromethane. After drying, evaporation of the dichloromethane and purification by chromatography on a silica column, Compound 1(2.12 g; 41%; m.p. 93° C.) is obtained.

Workup

  1. temperatureto reflux for 8 hours
  2. customThe solvent is then evaporated off
  3. extractionextracted with dichloromethane
  4. customAfter drying
  5. customevaporation of the dichloromethane and purification by chromatography on a silica column

Sources & evidence

ORD record
ord-cbc78a70f2714379b400ab1d2faa5ff6
Source dataset
uspto-grants-1990_03
Patent number
US04908375

Reaction notes

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