Ammonium thiocyanate → 2-(N-methyl-N-(2-methylphenyl)amino)-4H-pyrido[3,2-e]-1,3-thiazin-4-one

HRID 367170Notes

Reaction equation

HRID 367170 reaction equation
Cl[C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.S(Cl)(Cl)=O.[S-:15][C:16]#[N:17].[NH4+].[CH3:19][NH:20][C:21]1[C:22]([CH3:27])=[CH:23][CH:24]=[CH:25][CH:26]=1>CC(C)=O.CN(C=O)C>[CH3:19][N:20]([C:16]1[S:15][C:2]2[N:10]=[CH:9][CH:8]=[CH:7][C:3]=2[C:4](=[O:6])[N:17]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[CH3:27]

Participants

7

Reactant 4

HCID 15666Ammonium thiocyanateHCID 24386Thionyl ChlorideHCID 691372,N-DimethylanilineHCID 762582-Chloronicotinic acid

Product 1

HCID 232875672-(N-methyl-N-(2-methylphenyl)amino)-4H-pyrido[3,2-e]-1,3-thiazin-4-oneYield 80.6%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 6228DimethylformamideSolvent

Procedure

The reaction procedure of Example 57 was followed except that 1.613 mg (10.24 mmol) of 2-chloronicotinic acid, 15 ml of thionyl chloride, two droplets of DMF, 780 mg of ammonium thiocyanate, 15 ml of acetone, 1.21 g of N-methyl-o-toluidine and 10 ml of acetone were used. The resulting crude product was then recrystallized from ethanol to obtain 2.28 g of 2-(N-methyl-N-(2-methylphenyl)amino)-4H-pyrido[3,2-e]-1,3-thiazin-4-one.

Workup

  1. customThe reaction procedure of Example 57
  2. customThe resulting crude product was then recrystallized from ethanol

Sources & evidence

ORD record
ord-21701bb80e1e4b8ba8df499586c9693e
Source dataset
uspto-grants-2000_10
Patent number
US06133258

Reaction notes

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