Methyl isothiocyanate → HCID 178488243, compound

HRID 500544Notes

Reaction equation

HRID 500544 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][N:12]=1)[C:6]([NH:8][NH2:9])=O.[CH3:13][N:14]=[C:15]=[S:16].[OH-].[Na+]>O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:6]2[N:14]([CH3:13])[C:15]([SH:16])=[N:9][N:8]=2)[CH:10]=[CH:11][N:12]=1

Participants

5

Reactant 3

HCID 11167Methyl isothiocyanateHCID 14798Sodium HydroxideHCID 3225512-Methoxyisonicotinohydrazide

Product 1

HCID 178488243HCID 178488243, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

The title compound of example 23.1 (18.35 g, 109.8 mmol) and methyl isothiocyanate (8.83 g, 120 mmol) were stirred together at 60° C. for 30 minutes. Sodium hydroxide (4.83 g, 120 mmol) in water (32 mL) was added to the reaction mixture it was allowed to continue to stir at 60° C. for 12 hours. The reaction mixture was concentrated and diluted with water. It was acidified to pH 4-5 with 3 M HCl. A solid precipitated out which was filtered, washing with portions of water, then dried to afford the product as a beige solid (21.2 g, 87%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with water
  3. customA solid precipitated out which
  4. filtrationwas filtered
  5. washwashing with portions of water
  6. customdried

Sources & evidence

ORD record
ord-c51b3d4008d2404abf5a551ade3cdcf0
Source dataset
uspto-grants-2010_08
Patent number
US07772235B2

Reaction notes

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