Methyl isothiocyanate → HCID 178481695, compound

HRID 500551Notes

Reaction equation

HRID 500551 reaction equation
[CH3:1][N:2]1[CH:7]=[CH:6][C:5]([C:8]([NH:10][NH2:11])=O)=[CH:4][C:3]1=[O:12].[CH3:13][N:14]=[C:15]=[S:16].[OH-].[Na+]>CO.O>[SH:16][C:15]1[N:14]([CH3:13])[C:8]([C:5]2[CH:6]=[CH:7][N:2]([CH3:1])[C:3](=[O:12])[CH:4]=2)=[N:10][N:11]=1

Participants

6

Reactant 3

HCID 11167Methyl isothiocyanateHCID 14798Sodium HydroxideHCID 431322131-Methyl-2-oxo-1,2-dihydropyridine-4-carbohydrazide

Product 1

HCID 178481695HCID 178481695, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

The title compound of example 31.1 (1.0 g, 5.98 mmol) was stirred in methanol (6 mL) at 60° C. Methyl isothiocyanate (481 mg, 6.58 mmol) was dissolved in methanol (2 mL) and added to the reaction mixture which was stirred for 15 min. After 15 min a solution of sodium hydroxide (263 mg) in water (2 mL) was added to the reaction mixture which was kept stirring at 60° C. overnight. The reaction mixture was then concentrated in vacuo to remove the methanol and the remaining residue was stirred in 3 M HCl (aq) to precipitate the product which was collected by vacuum filtration (off-white powder, 1.2 g, 90%).

Workup

  1. additionadded to the reaction mixture which
  2. stirringwas kept stirring at 60° C. overnight
  3. concentrationThe reaction mixture was then concentrated in vacuo
  4. customto remove the methanol
  5. stirringthe remaining residue was stirred in 3 M HCl (aq)
  6. customto precipitate the product which
  7. filtrationwas collected by vacuum filtration (off-white powder, 1.2 g, 90%)

Sources & evidence

ORD record
ord-129aadb9c7d34d17b680ea2e3404fd0a
Source dataset
uspto-grants-2010_08
Patent number
US07772235B2

Reaction notes

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