Methyl isothiocyanate → HCID 178481696, compound

HRID 500541Notes

Reaction equation

HRID 500541 reaction equation
[O:1]=[C:2]1[CH:7]=[C:6]([C:8]([NH:10][NH2:11])=O)[CH:5]=[CH:4][N:3]1[CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17].[CH3:20][N:21]=[C:22]=[S:23]>CO.O>[SH:23][C:22]1[N:21]([CH3:20])[C:8]([C:6]2[CH:5]=[CH:4][N:3]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[C:2](=[O:1])[CH:7]=2)=[N:10][N:11]=1

Participants

5

Reactant 2

HCID 11167Methyl isothiocyanateHCID 684588242-Oxo-1-(2-trimethylsilanyl-ethoxymethyl)-1,2-dihydro-pyridine-4-carboxylic acid hydrazide

Product 1

HCID 178481696HCID 178481696, compoundYield 105.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

The title compound of Example 20.1 (19.0 g, 67.0 mmol) was stirred in methanol (150 mL) and heated to 60° C. Methyl isothiocyanate (5.04 mL, 73.7 mmol) was then added via a syringe. After stirring for 40 minutes, a solution on NaOH (2.95 g, 73.7 mmol) in water (30 mL) was added and the reaction mixture was stirred at 60° C. overnight. The reaction mixture was cooled to room temperature and concentrated. The aqueous residue was neutralized, extracted with chloroform, and the organic layer dried over sodium sulfate and concentrated. The residue was purified by silica gel using ethyl acetate to give the product (24.0 g, 56%).

Workup

  1. stirringthe reaction mixture was stirred at 60° C. overnight
  2. temperatureThe reaction mixture was cooled to room temperature
  3. concentrationconcentrated
  4. extractionextracted with chloroform
  5. dry with materialthe organic layer dried over sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel

Sources & evidence

ORD record
ord-551fe588aac344159b1086df724037fe
Source dataset
uspto-grants-2010_08
Patent number
US07772235B2

Reaction notes

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