Hydrochloric Acid → HCID 178510476, compound

HRID 714443Notes

Reaction equation

HRID 714443 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=2)[C:5]([C:17]#[N:18])=[C:4]([S:19]C2C=CC=CC=2)[N:3]=1.[S-2].[Na+].[Na+].Cl>CN(C=O)C>[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=2)[C:5]([C:17]#[N:18])=[C:4]([SH:19])[N:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14804Sodium SulfideHCID 11393845HCID 11393845, compound

Product 1

HCID 178510476HCID 178510476, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

2 g (5.77 mmol) of 2-amino-4-(3-fluorophenyl)-6-(phenylsulfanyl)pyridine-3,5-dicarbonitrile (Example 37A) were initially charged in 20 ml of DMF. 1.58 g (20.21 mmol) of sodium sulfide were added, and the mixture was stirred at 80° C. for 2 h and stirred further at RT overnight. 10 ml of 1N hydrochloric acid were added to the reaction mixture, and the precipitate was filtered off, washed with water and dried under high vacuum. In addition, more solid precipitated from the filtrate overnight, and this solid was filtered off and washed with water. Once more, this gave the desired solid.

Workup

  1. stirringstirred further at RT overnight
  2. filtrationthe precipitate was filtered off
  3. washwashed with water
  4. customdried under high vacuum
  5. customIn addition, more solid precipitated from the filtrate overnight
  6. filtrationthis solid was filtered off
  7. washwashed with water
  8. customOnce more, this gave the desired solid

Sources & evidence

ORD record
ord-56981cb760714ba5b5e4e6c034c5d1d1
Source dataset
uspto-grants-2015_11
Patent number
US09187428B2

Reaction notes

Loading…