Hydrochloric Acid → HCID 178483863, compound

HRID 2362815Notes

Reaction equation

HRID 2362815 reaction equation
[S-2].[Na+].[Na+].[NH2:4][C:5]1[C:10]([C:11]#[N:12])=[C:9]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][N:22]([CH3:24])[CH3:23])=[CH:15][CH:14]=2)[C:8]([C:25]#[N:26])=[C:7]([S:27]CC2C=CC=CC=2)[N:6]=1.Cl.O>CN(C=O)C>[NH2:4][C:5]1[C:10]([C:11]#[N:12])=[C:9]([C:13]2[CH:14]=[CH:15][C:16]([O:19][CH2:20][CH2:21][N:22]([CH3:24])[CH3:23])=[CH:17][CH:18]=2)[C:8]([C:25]#[N:26])=[C:7]([SH:27])[N:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962Water2×HCID 14804Sodium SulfideHCID 687062052-Amino-6-(benzylthio)-4-{4-[2-(dimethylamino)ethoxy]phenyl}pyridine-3,5-dicarbonitrile

Product 1

HCID 178483863HCID 178483863, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.97 g (12.41 mmol) of sodium sulphide is added to a solution of 3.56 g (8.28 mmol) of the compound from Example 33A in 13 ml of dry DMF. The reaction mixture is stirred at +80° C. for 2 h. After cooling to RT, 2 ml of 37% strength hydrochloric acid are added to the reaction mixture, whose temperature rises to 65° C. After addition of 2.6 ml of water, the reaction mixture is cooled back to RT. After addition of a further 5 ml of water, the mixture is washed with 5 ml of ethyl acetate and made alkaline by addition of 40% strength sodium hydroxide solution. Yellow crystals precipitate, and these are filtered off with suction, washed with 10 ml of water and 10 ml of diethyl ether and then dried under reduced pressure. The filtrate is concentrated using a rotary evaporator and stirred with a little water. The resulting crystals are filtered off with suction, washed with in each case 10 ml of water and diethyl ether and dried under reduced pressure.

Workup

  1. customrises to 65° C
  2. temperaturethe reaction mixture is cooled back to RT
  3. washthe mixture is washed with 5 ml of ethyl acetate
  4. additionby addition of 40% strength sodium hydroxide solution
  5. filtrationYellow crystals precipitate, and these are filtered off with suction
  6. washwashed with 10 ml of water and 10 ml of diethyl ether
  7. customdried under reduced pressure
  8. concentrationThe filtrate is concentrated
  9. customa rotary evaporator
  10. stirringstirred with a little water
  11. filtrationThe resulting crystals are filtered off with suction
  12. washwashed with in each case 10 ml of water and diethyl ether
  13. customdried under reduced pressure

Sources & evidence

ORD record
ord-4b55f0e44de341b9b56098f46f6f5b81
Source dataset
uspto-grants-2014_04
Patent number
US08691850B2

Reaction notes

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