Methyl iodide → HCID 12044319, compound

HRID 1595161Notes

Reaction equation

HRID 1595161 reaction equation
[CH3:1][C:2](C)([O-:4])[CH3:3].[K+].C1OCCOCCOCCOCCOCCOC1.[CH3:25][C:26]1[C:30]2[C:31](=[O:37])[NH:32][CH2:33]CC(=O)[C:29]=2[NH:28][CH:27]=1.CI>C1COCC1.CN(C=O)C>[CH3:29][N:28]1[C:3]2[C:2](=[O:4])[CH2:1][CH2:33][NH:32][C:31](=[O:37])[C:30]=2[C:26]([CH3:25])=[CH:27]1

Participants

7

Reactant 4

HCID 6328Methyl iodide3×HCID 2855718-Crown-6HCID 12146430HCID 12146430, compoundHCID 23665647Potassium tert-butoxide3×

Product 1

HCID 12044319HCID 12044319, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8028TetrahydrofuranSolvent3×

Procedure

To a suspension of potassium t-butoxide (1.62 g, 14.4 mmole) and 18-crown-6 (317 mg, 1.2 mmole) in THF (20 ml), a suspension of 3-methyl-1,4,5,6,7,8-hexahydropyrrolo[3,2-c]azepine-4,8-dione (2.12 g, 12 mmole) in THF (20 ml) and a solution of methyl iodide (2.55 g, 18 mmole) in THF (5 ml) were successively added dropwise, and the reaction mixture was stirred at room temperature. Twenty-four hours later, a solution of-potassium t-butoxide (0.81 g, 7.2 mmole) and methyl iodide (1.28 g, 9.0 mmole) in DMF (5 ml) was added, and 24 hours later, a solution of potassium t-butoxide (0.81 g, 7.2 mmole) and methyl iodide (1.28 g, 9 mmole) in DMF (5 ml) was added further. The reaction mixture was then stirred at room temperature for 3 hours.

Workup

  1. stirringThe reaction mixture was then stirred at room temperature for 3 hours

Sources & evidence

ORD record
ord-eb08236a36194be8a83a36df0d8978f3
Source dataset
uspto-grants-2001_09
Patent number
US06288056B1

Reaction notes

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