Water → N-(3,5-Dimethylphenyl)-2-thioxo-1,2-dihydropyridine-3-carboxamide

HRID 1984707Notes

Reaction equation

HRID 1984707 reaction equation
[SH:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.C(N1C=CN=C1)(N1C=CN=C1)=O.O.[NH2:24][C:25]1[CH:30]=[C:29]([CH3:31])[CH:28]=[C:27]([CH3:32])[CH:26]=1>CN(C)C=O>[CH3:32][C:27]1[CH:26]=[C:25]([NH:24][C:4]([C:3]2[C:2](=[S:1])[NH:10][CH:9]=[CH:8][CH:7]=2)=[O:6])[CH:30]=[C:29]([CH3:31])[CH:28]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 79493,5-DimethylanilineHCID 682631,1'-CarbonyldiimidazoleHCID 178524460HCID 178524460, compound

Product 1

HCID 23151038N-(3,5-Dimethylphenyl)-2-thioxo-1,2-dihydropyridine-3-carboxamideYield 89%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Mercaptonicotinic acid (90 g, 0.58 mol) was suspended in N,N-dimethylformamide (660 mL), and carbonyldiimidazole (110 g, 0.70 mol) was added thereto under ice-cooling, and then the mixture was stirred at room temperature for 2 hours. Water (5.4 mL) was added thereto, the whole was stirred for 40 minutes. 3,5-Xylidine (76 mL, 0.61 mol) was added thereto, and the mixture was stirred for 16 hours at 60° C. The mixture was allowed to stand, water (1.3 L) was added thereto, and then the precipitated solid was filtered off. The solid was dried under reduced pressure at 45° C. to give 130 g of the title reference compound as a yellow solid. (Yield 89%)

Workup

  1. temperatureunder ice-cooling
  2. stirringthe whole was stirred for 40 minutes
  3. stirringthe mixture was stirred for 16 hours at 60° C
  4. filtrationthe precipitated solid was filtered off
  5. customThe solid was dried under reduced pressure at 45° C.
  6. customto give 130 g of the title reference compound as a yellow solid

Sources & evidence

ORD record
ord-863883d02ac144628c01ac369dcc7108
Source dataset
uspto-grants-2009_06
Patent number
US07544703B2

Reaction notes

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