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

HRID 367172Notes

Reaction equation

HRID 367172 reaction equation
Cl[C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].S(Cl)(Cl)=O.[S-:15][C:16]#[N:17].[NH4+].[CH3:19][NH:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][C:28]([F:31])([F:30])[F:29])=[CH:23][CH:22]=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:5])[N:17]=1)[C:21]1[CH:26]=[CH:25][C:24]([O:27][C:28]([F:29])([F:30])[F:31])=[CH:23][CH:22]=1

Participants

7

Reactant 4

HCID 15666Ammonium thiocyanateHCID 24386Thionyl ChlorideHCID 737351n-Methyl-4-(trifluoromethoxy)anilineHCID 27745412-Chloronicotinoyl chloride

Product 1

HCID 232876422-[N-methyl-N-(4-trifluoromethoxylphenyl)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 824 mg (5.23 mmol) of 2-chloronicotinoyl chloride, 10 ml of thionyl chloride, two droplets off DMF, 400 mg of ammonium thiocyanate, 10 ml of acetone, 1.0 g of N-methyl-4-trifluoromethoxyaniline and 10 ml of acetone were used. The resulting crude product was then recrystallized from ethanol to obtain 1.49 g of 2-[N-methyl-N-(4-trifluoromethoxylphenyl)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-624f4fc3b6044c73ab48091c28236816
Source dataset
uspto-grants-2000_10
Patent number
US06133258

Reaction notes

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