Hydrochloric Acid → HCID 178494293, compound

HRID 1500101Notes

Reaction equation

HRID 1500101 reaction equation
Cl[C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][OH:19])=[CH:12][CH:11]=2)[C:5]([C:20]#[N:21])=[C:4]([O:22][CH3:23])[N:3]=1.[S-2:24].[Na+].[Na+].O.Cl>CN(C=O)C.CO>[OH:19][CH2:18][CH2:17][O:16][C:13]1[CH:14]=[CH:15][C:10]([C:6]2[C:7]([C:8]#[N:9])=[C:2]([SH:24])[N:3]=[C:4]([O:22][CH3:23])[C:5]=2[C:20]#[N:21])=[CH:11][CH:12]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14804Sodium SulfideHCID 86654213HCID 86654213, compound

Product 1

HCID 178494293HCID 178494293, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

4.0 g (12.1 mmol) of 2-chloro-4-[4-(2-hydroxyethoxy)phenyl]-6-methoxypyridine-3,5-dicarbonitrile are dissolved in 16 ml of anhydrous DMF, 1.42 g (18.2 mmol) of anhydrous sodium sulphide are added and the mixture is stirred at room temperature for 2 h. 36 ml of water are added, and with stirring the solution is slowly added dropwise to a mixture, warmed to 50° C., of 61 ml of 1M hydrochloric acid and 20 ml of methanol. The yellow suspension is stirred at RT for 1 h and filtered off with suction, and the precipitate is washed with water and dried at 45° C. under reduced pressure overnight.

Workup

  1. stirringwith stirring the solution
  2. additionis slowly added dropwise to a mixture
  3. stirringThe yellow suspension is stirred at RT for 1 h
  4. filtrationfiltered off with suction
  5. washthe precipitate is washed with water
  6. customdried at 45° C. under reduced pressure overnight

Sources & evidence

ORD record
ord-12585e9ec53d45b2b4925ade249d7ccf
Source dataset
uspto-grants-2015_12
Patent number
US09205077B2

Reaction notes

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