Water → HCID 178456766, compound

HRID 595423Notes

Reaction equation

HRID 595423 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([NH:12][CH:13]([CH3:15])[CH3:14])[C:5]([C:6]([NH:8][NH2:9])=[O:7])=[CH:4][N:3]=1.O.[OH-].[K+].[C:19](=S)=[S:20]>CCO>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([C:6]2[O:7][C:19]([SH:20])=[N:9][N:8]=2)=[C:10]([NH:12][CH:13]([CH3:15])[CH3:14])[CH:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6348Carbon DisulfideHCID 14797Potassium HydroxideHCID 896896686-Chloro-4-(isopropylamino)nicotinohydrazide

Product 1

HCID 178456766HCID 178456766, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

6-chloro-4-(isopropylamino)nicotinohydrazide (10) (1.5 g, 8.7 mmol) was taken in EtOH (10 mL): H2O (5 mL). Added KOH (13 mmol, 1.5 equiv.) followed by the addition of CS2 (87 mmol, 10 equiv.) to the reaction mixture and heated at 90° C., overnight. The reaction mass was concentrated under reduced pressure to remove solvents from the reaction mixture. The crude material obtained was taken to next step as such without purification. LC/MS: Purospher@star RP-18, 4×55 mm, 3 μm; Solvent A=10% ACN: 90% H2O: 20 mM NH4OAc; Solvent B=90% ACN: 10% H2O: 20 mM NH4COOAc; gradient 0-100% B over 1.5 min (3.2 min run time); retention time: 1.27 min; LCMS (ES-API), m/z 269.0 (M−H).

Workup

  1. concentrationThe reaction mass was concentrated under reduced pressure
  2. customto remove solvents from the reaction mixture

Sources & evidence

ORD record
ord-fde6a55566924b978a98d227d580bf38
Source dataset
uspto-grants-2016_01
Patent number
US09242975B2

Reaction notes

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