Acetone → HCID 941901, compound

HRID 367156Notes

Reaction equation

HRID 367156 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[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[CH3:27]C(C)=O>CN(C=O)C>[CH2:19]([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][CH:22]=1)[CH3:27]

Participants

7

Reactant 5

HCID 180Acetone2×HCID 7515N-MethylanilineHCID 15666Ammonium thiocyanateHCID 24386Thionyl ChlorideHCID 762582-Chloronicotinic acid

Product 1

HCID 941901HCID 941901, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The reaction procedure of Example 57 was followed except that 1.757 g (11.2 mmol) of 2-chloronicotinic acid, 15 ml of thionyl chloride, two droplets of DMF, 891 mg of ammonium thiocyanate, 15 ml of acetone, 1.26 g of N-methylaniline and 10 ml of acetone were used. The product was then recrystallized from ethanol to obtain 2.37 g of 2-(N-ethyl-N-phenylamino)-4H-pyrido[3,2-e]-1,3-thiazin-4-one.

Workup

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

Sources & evidence

ORD record
ord-63a24ecd4ded4da28945fbbcd9476100
Source dataset
uspto-grants-2000_10
Patent number
US06133258

Reaction notes

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