Methyl iodide → HCID 178503951, compound

HRID 1054985Notes

Reaction equation

HRID 1054985 reaction equation
[CH3:1][C:2]([CH3:15])=[CH:3][C:4]([NH:6][C:7]([N:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)=[S:8])=[O:5].[C:16](=O)([O-])[O-].[Na+].[Na+].IC>O1CCCC1>[CH3:16][S:8]/[C:7](=[N:6]\[C:4](=[O:5])[CH:3]=[C:2]([CH3:15])[CH3:1])/[N:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10340Sodium CarbonateHCID 900174853-methyl-N-(piperidine-1-carbonothioyl)but-2-enamide

Product 1

HCID 178503951HCID 178503951, compoundYield 151%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3-methyl-N-(piperidine-1-carbonothioyl)but-2-enamide (3.21 g, 14.2 mmol, Eq: 1.00), sodium carbonate (1.58 g, 14.9 mmol, Eq: 1.05) and iodomethane (10.1 g, 4.43 ml, 70.9 mmol, Eq: 5) in tetrahydrofuran (100 ml) was stirred for 2.5 days under reflux. The mixture was evaporated, 30 ml of ethyl acetate was added and the mixture was filtrated, the filtrate was evaporated affording 3-methyl-but-2-enoic acid 1-methylsulfanyl-1-piperidin-1-yl-meth-(Z)-ylideneamide (5.137 g, 151%) as an orange-brown semi-solid. MS: m/z=241.2 (M+H+)

Workup

  1. temperatureunder reflux
  2. customThe mixture was evaporated
  3. addition30 ml of ethyl acetate was added
  4. filtrationthe mixture was filtrated
  5. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-8c5aa53044454fd592de83080465e964
Source dataset
uspto-grants-2016_07
Patent number
US09394311B2

Reaction notes

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