Thionyl Chloride → 2-(1,2,3,4-tetrahydroquinolin-1-yl)-4H-pyrido[3,2-e]-1,3-thiazin-4-one monohydrate

HRID 367178Notes

Reaction equation

HRID 367178 reaction equation
Cl[C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(Cl)(Cl)=O.[N-:15]=[C:16]=[S:17].[NH4+].Br[C:20]1[CH:21]=[C:22]2[C:27](=[C:28](Br)[CH:29]=1)[NH:26][CH2:25][CH2:24][CH2:23]2>CC(C)=O.CN(C=O)C>[OH2:5].[N:26]1([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)[C:27]2[C:22](=[CH:21][CH:20]=[CH:29][CH:28]=2)[CH2:23][CH2:24][CH2:25]1

Participants

7

Reactant 4

HCID 24386Thionyl ChlorideHCID 762582-Chloronicotinic acidHCID 232876446,8-Dibromo-1,2,3,4-tetrahydroquinolineHCID 178514171HCID 178514171, compound

Product 1

HCID 232876382-(1,2,3,4-tetrahydroquinolin-1-yl)-4H-pyrido[3,2-e]-1,3-thiazin-4-one monohydrateYield 84.3%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 6228DimethylformamideSolvent

Procedure

The reaction procedure of Example 57 was followed except that 1.339 g (8.5 mmol) of 2-chloronicotinic acid, 13 ml of thionyl chloride, two droplets of DMF, 680 mg of ammonium isothiocyanate, 13 ml of acetone, 2.473 g of 6,8-dibromo-1,2,3,4-tetrahydroquinoline and 8 ml of acetone were used. The product was then recrystallized from a mixture of ethanol and hexane to obtain 2.244 g of 2-(1,2,3,4-tetrahydroquinolin-1-yl)-4H-pyrido[3,2-e]-1,3-thiazin-4-one monohydrate.

Workup

  1. customThe reaction procedure of Example 57
  2. customThe product was then recrystallized from a mixture of ethanol and hexane

Sources & evidence

ORD record
ord-8c653e1fff9c4f9fa8e057e880f88459
Source dataset
uspto-grants-2000_10
Patent number
US06133258

Reaction notes

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