methyl 2-cyanonicotinate → HCID 19862615, compound

HRID 1165164Notes

Reaction equation

HRID 1165164 reaction equation
C[O-].[Na+].[C:4]([C:6]1[N:15]=[CH:14][CH:13]=[CH:12][C:7]=1[C:8]([O:10][CH3:11])=[O:9])#[N:5].[Cl:16][C:17]1[CH:18]=[C:19]([C:23]2[S:24][CH:25]=[C:26](CO)[N:27]=2)[CH:20]=[CH:21][CH:22]=1>C1(C)C=CC=CC=1>[C:4]([C:6]1[N:15]=[CH:14][CH:13]=[CH:12][C:7]=1[C:8]([O:10][CH2:11][C:26]1[N:27]=[C:23]([C:19]2[CH:20]=[CH:21][CH:22]=[C:17]([Cl:16])[CH:18]=2)[S:24][CH:25]=1)=[O:9])#[N:5]

Participants

5

Reactant 3

HCID 339115methyl 2-cyanonicotinateHCID 10942334Sodium MethoxideHCID 14330272[2-(3-Chlorophenyl)-1,3-thiazol-4-yl]methanol

Product 1

HCID 19862615HCID 19862615, compoundYield 25.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Sodium methylate (0.11 g; 0.002 mole) is added to a solution of methyl 2-cyanonicotinate (3.24 g; 0.02 mole) and 2-(3-chlorophenyl)-4-(hydroxymethyl)thiazole (4.96 g; 0.022 mole) in toluene (100 cc). The methanol/toluene azeotrope is distilled off and the toluene is then evaporated off. The residue is treated with water. The precipitate formed is filtered off, washed with water and then dried. Compound 2 (1.8 g; 25% m.p. 130° C.) is obtained.

Workup

  1. distillationThe methanol/toluene azeotrope is distilled off
  2. customthe toluene is then evaporated off
  3. additionThe residue is treated with water
  4. customThe precipitate formed
  5. filtrationis filtered off
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-77eb3f77bea946e49e5d3dd9a4f13441
Source dataset
uspto-grants-1990_03
Patent number
US04908375

Reaction notes

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