Thionyl Chloride → 2-[N-(3,4-dimethoxyphenyl)-N-ethylaminoj-4H-pyrido[3,2-e]-1,3-thiazin-4-one

HRID 367181Notes

Reaction equation

HRID 367181 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.[N-:15]=[C:16]=[S:17].[NH4+].[CH3:19][O:20][C:21]1[CH:22]=[C:23]([CH:27]=[CH:28][C:29]=1[O:30][CH3:31])[NH:24][CH2:25][CH3:26]>CC(C)=O.CN(C=O)C>[CH3:19][O:20][C:21]1[CH:22]=[C:23]([N:24]([C:16]2[S:17][C:2]3[N:10]=[CH:9][CH:8]=[CH:7][C:3]=3[C:4](=[O:6])[N:15]=2)[CH2:25][CH3:26])[CH:27]=[CH:28][C:29]=1[O:30][CH3:31]

Participants

7

Reactant 4

HCID 24386Thionyl ChlorideHCID 762582-Chloronicotinic acidHCID 12686507N-Ethyl-3,4-dimethoxyanilineHCID 178514171HCID 178514171, compound

Product 1

HCID 232876172-[N-(3,4-dimethoxyphenyl)-N-ethylaminoj-4H-pyrido[3,2-e]-1,3-thiazin-4-oneYield 89.7%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 6228DimethylformamideSolvent

Procedure

The reaction procedure of Example 85 was followed except that 1.733 g (11 mmol) of 2-chloronicotinic acid, 15 ml of thionyl chloride, two droplets of DMF, 880 mg of ammonium isothiocyanate, 15 ml of acetone, 1.993 g of 3,4-dimethoxy-N-ethylaniline and 10 ml of acetone were used. The product was then recrystallized from ethanol to obtain 3.388 g of 2-[N-(3,4-dimethoxyphenyl)-N-ethylaminoj-4H-pyrido[3,2-e]-1,3-thiazin-4-one.

Workup

  1. customThe reaction procedure of Example 85
  2. customThe product was then recrystallized from ethanol

Sources & evidence

ORD record
ord-a67016b7aeaa465c85041181d0425e01
Source dataset
uspto-grants-2000_10
Patent number
US06133258

Reaction notes

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