Ammonium thiocyanate → HCID 23287729, compound

HRID 367192Notes

Reaction equation

HRID 367192 reaction equation
[S-]C#N.[NH4+].Cl[C:6]1[C:11]([C:12]([N:14]=[C:15]=[S:16])=[O:13])=[CH:10][N:9]=[CH:8][CH:7]=1.[Cl:17][C:18]1[CH:25]=[CH:24][C:21]([NH:22][CH3:23])=[CH:20][CH:19]=1>CC(C)=O.C1COCC1>[Cl:17][C:18]1[CH:25]=[CH:24][C:21]([N:22]([C:15]2[S:16][C:6]3[CH:7]=[CH:8][N:9]=[CH:10][C:11]=3[C:12](=[O:13])[N:14]=2)[CH3:23])=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 15666Ammonium thiocyanateHCID 702724-Chloro-N-methylbenzenamineHCID 23287680HCID 23287680, compound

Product 1

HCID 23287729HCID 23287729, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent3×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 1.416 g (8.99 mmol) of 4-chloronicotinic acid, 15 ml of thionyl chloride and two droplets of DMF was heated under reflux for 2 hours. The reaction mixture was allowed to cool, and then concentrated under reduced pressure to obtain 4-chloronicotinoyl chloride. The compound thus obtained was then suspended in a mixture of 10 ml of acetone and 10 ml of THF. The suspension thus obtained was then added dropwise to a solution of 753 mg of ammonium thiocyanate in 15 ml of acetone with stirring in 5 minutes. After the termination of dropwise addition, the reaction mixture was heated to a temperature of 40° C. with stirring for 6 minutes to obtain a mixture containing 4-chloronicotinoyl isothiocyanate. To the mixture thus obtained was then added dropwise a solution of 1.55 g of 4-chloro-N-methylaniline in 10 ml of acetone with stirring in 5 minutes. The reaction mixture was stirred at room temperature for 17 hours, concentrated to half the initial volume under reduced pressure, and then poured into about 500 ml of ice-water. The resulting crystal was collected by filtration, washed with water, and then dried under reduced pressure. The resulting crude product was purified through silica gel column chromatography (eluant: CHCl3 +1 to 3% methanol), and then recrystallized from ethanol to obtain 717 mg of 2-[N-(4-chlorophenyl)-N-methylamino]-4H-pyrido[3,4-e]-1,3-thiazin-4-one.

Workup

  1. customThe compound thus obtained
  2. customThe suspension thus obtained
  3. additionAfter the termination of dropwise addition
  4. stirringwith stirring for 6 minutes
  5. customto obtain a mixture
  6. customTo the mixture thus obtained
  7. stirringwith stirring in 5 minutes
  8. stirringThe reaction mixture was stirred at room temperature for 17 hours
  9. concentrationconcentrated to half the initial volume under reduced pressure
  10. additionpoured into about 500 ml of ice-water
  11. filtrationThe resulting crystal was collected by filtration
  12. washwashed with water
  13. customdried under reduced pressure
  14. customThe resulting crude product was purified through silica gel column chromatography (eluant: CHCl3 +1 to 3% methanol)
  15. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-bd5e78253fd943719feca2aad131413f
Source dataset
uspto-grants-2000_10
Patent number
US06133258

Reaction notes

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