Hydrochloric Acid → HCID 86691916, compound

HRID 714464Notes

Reaction equation

HRID 714464 reaction equation
N[C:2]1[N:7]=[C:6]([S:8][CH2:9][C:10]2[CH:11]=[C:12]([C:16]([NH:18][CH3:19])=[O:17])[CH:13]=[CH:14][CH:15]=2)[C:5]([C:20]#[N:21])=[C:4]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:3]=1[C:28]#[N:29].[ClH:30].N([O-])=O.[Na+].[OH-].[Na+]>O>[Cl:30][C:2]1[N:7]=[C:6]([S:8][CH2:9][C:10]2[CH:11]=[C:12]([C:16]([NH:18][CH3:19])=[O:17])[CH:13]=[CH:14][CH:15]=2)[C:5]([C:20]#[N:21])=[C:4]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:3]=1[C:28]#[N:29]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 23668193Sodium NitriteHCID 66631239HCID 66631239, compound

Product 1

HCID 86691916HCID 86691916, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

1.72 g (4.3 mmol) of 3-{[(6-amino-3,5-dicyano-4-phenylpyridin-2-yl)sulfanyl]methyl}-N-methylbenzenecarboxamide Example 9 were dissolved in ice-cooled conc. hydrochloric acid. 0.89 g (12.89 mmol) of sodium nitrite was added, and the mixture was then stirred at 0° C. for 1 h and at RT overnight. After 1 h, a precipitate had already formed. With cooling, 100 ml of water were added to the reaction mixture, and the pH was adjusted carefully to pH 7 using conc. aqueous sodium hydroxide solution. The precipitate was filtered off.

Workup

  1. waitAfter 1 h
  2. customa precipitate had already formed
  3. temperatureWith cooling
  4. filtrationThe precipitate was filtered off

Sources & evidence

ORD record
ord-19693d2f27004be297339ee4c5b15b6b
Source dataset
uspto-grants-2015_11
Patent number
US09187428B2

Reaction notes

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