Methyl iodide → HCID 178503950, compound

HRID 1054923Notes

Reaction equation

HRID 1054923 reaction equation
[CH3:1][C:2]([CH3:14])=[CH:3][C:4]([NH:6][C:7]([N:9]1[CH2:13][CH2:12][CH2:11][CH2:10]1)=[S:8])=[O:5].[C:15](=O)([O-])[O-].[Na+].[Na+].IC>O1CCCC1>[CH3:15][S:8]/[C:7](=[N:6]\[C:4](=[O:5])[CH:3]=[C:2]([CH3:14])[CH3:1])/[N:9]1[CH2:10][CH2:11][CH2:12][CH2:13]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10340Sodium CarbonateHCID 900178533-methyl-N-(pyrrolidine-1-carbonothioyl)but-2-enamide

Product 1

HCID 178503950HCID 178503950, compoundYield 48.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 3-methyl-N-(pyrrolidine-1-carbonothioyl)but-2-enamide (230 mg, 1.08 mmol, Eq: 1.00), sodium carbonate (121 mg, 1.14 mmol, Eq: 1.05) and iodomethane (769 mg, 339 μl, 5.42 mmol, Eq: 5) in tetrahydrofuran (7 ml) was stirred for 18 hours at 70° C. The crude material was applied on silicagel and purified by flash chromatography over a 20 g silicagel column using heptane/ethyl acetate 50-100% as eluent affording 3-methyl-but-2-enoic acid 1-methylsulfanyl-1-pyrrolidin-1-yl-meth-(Z)-ylideneamide (119 mg/48.5%) as a light yellow liquid. MS: m/e=227.1 (M+H+)

Workup

  1. custompurified by flash chromatography over a 20 g silicagel column

Sources & evidence

ORD record
ord-acd99be5a1024cbc8fa5c1cd4d8df127
Source dataset
uspto-grants-2016_07
Patent number
US09394311B2

Reaction notes

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