Methyl iodide → HCID 66755678, compound

HRID 1642136Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([NH:12][C:13]2([C:19]([O:21][CH3:22])=[O:20])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)(=[O:11])=[O:10])=[CH:5][CH:4]=1.[C:23]([O-])([O-])=O.[K+].[K+].CI.CCCCCCC.C(OCC)(=O)C>CC(C)=O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([S:9]([N:12]([C:13]2([C:19]([O:21][CH3:22])=[O:20])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[CH3:23])(=[O:10])=[O:11])=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 40 °C

Procedure

Methyl 1-(4-methoxyphenylsulfonamido)cyclohexanecarboxylate (27 g, 82.5 mmol) was dissolved in acetone (450 ml), and K2CO3 (22.8 g, 165 mmol) was added thereto. Methyl iodide (10.3 ml, 165 mmol) was then added, and the suspension was heated overnight at 40° C. in a closed flask. Because the reaction was not yet complete (TLC monitoring, heptane/ethyl acetate 2:1), methyl iodide (7.7 ml, 124 mmol) was again added and stirring was carried out over the weekend at room temperature. Methyl iodide (2.6 ml, 41.8 mmol) was again added, and stirring was carried out overnight at 40° C. After cooling, the solid materials were filtered off and the filtrate was concentrated to dryness. The crude product was used further without being purified further.

Workup

additionwas again added
customwas carried out over the weekend at room temperature
stirringstirring
temperatureAfter cooling
filtrationthe solid materials were filtered off
concentrationthe filtrate was concentrated to dryness
customwithout being purified further

Sources & evidence

ORD record: ord-f98b9bc638714af59e6c35c10eb2527b
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08119633B2

Reaction notes

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