N-Methylbenzylamine → HCID 23287647, compound

HRID 367174Notes

Reaction equation

HRID 367174 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][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CC(C)=O.CN(C=O)C>[CH2:21]([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)[CH3:19])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

7

Reactant 4

HCID 7669N-MethylbenzylamineHCID 15666Ammonium thiocyanateHCID 24386Thionyl ChlorideHCID 762582-Chloronicotinic acid

Product 1

HCID 23287647HCID 23287647, compoundYield 48.2%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×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, 1.42 g of N-methylbenzylamine and 10 ml of acetone were used. The resulting crude product was then recrystallized from a mixture of ethanol and ether to obtain 1.53 g of 2-(N-benzyl-N-methylamino)-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 a mixture of ethanol and ether

Sources & evidence

ORD record
ord-92436f738e4f4893afac34ad09176b7c
Source dataset
uspto-grants-2000_10
Patent number
US06133258

Reaction notes

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