N-Methylcyclohexylamine → HCID 23287725, compound

HRID 367176Notes

Reaction equation

HRID 367176 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][CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1>CC(C)=O.CN(C=O)C>[CH:21]1([N:20]([C:16]2[S:15][C:2]3[N:10]=[CH:9][CH:8]=[CH:7][C:3]=3[C:4](=[O:6])[N:17]=2)[CH3:19])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

7

Reactant 4

HCID 7514N-MethylcyclohexylamineHCID 15666Ammonium thiocyanateHCID 24386Thionyl ChlorideHCID 762582-Chloronicotinic acid

Product 1

HCID 23287725HCID 23287725, compoundYield 46.8%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 6228DimethylformamideSolvent

Procedure

The reaction procedure of Example 57 was followed except that 1.749 g (11.10 mmol) of 2-chloronicotinic acid, 15 ml of thionyl chloride, two droplets of DMF, 888 mg of ammonium thiocyanate, 15 ml of acetone, 1.32 g of N-methylcyclohexylamine and 10 ml of acetone were used. The resulting crude product was then recrystallized from ethanol to obtain 1.43 g of 2-(N-cyclohexyl-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 ethanol

Sources & evidence

ORD record
ord-636bb9cb69a7460c9933ea9c0004648a
Source dataset
uspto-grants-2000_10
Patent number
US06133258

Reaction notes

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