Dichloromethane → HCID 22631371, compound

HRID 2416589Notes

Reaction equation

HRID 2416589 reaction equation
CO[CH:3](OC)[CH2:4][N:5]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([I:23])=[C:19]([O:24][CH3:25])[CH:18]=1)S(C1C=CC(C)=CC=1)(=O)=O.ClCCl.CC(C)([O-])C.[K+]>O1CCOCC1.Cl.CN(C=O)C.C(O)(C)(C)C>[I:23][C:20]1[CH:21]=[C:22]2[C:17](=[CH:18][C:19]=1[O:24][CH3:25])[CH:16]=[N:5][CH:4]=[CH:3]2

Participants

8

Reactant 3

HCID 6344Dichloromethane2×HCID 22631326HCID 22631326, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 22631371HCID 22631371, compound

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolventHCID 6386tert-ButanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
40 °C

Procedure

20.5 g (39.6 mmol) of N-(2,2-dimethoxyethyl)-N-(4-iodo-3-methoxybenzyl)-4-methylbenzenesulfonamide was dissolved in a mixture of 240 ml of dioxane and 70 ml of 6 N hydrochloric acid, and the obtained solution was heated under reflux for 2 hours. After the treatment with dichloromethane as the extraction solvent in an ordinary manner, the obtained crude product was dissolved in a mixture of 100 ml of DMF and 100 ml of t-butyl alcohol. 2.54 g (22.6 mmol) of potassium t-butoxide was added to the obtained solution and they were stirred at 40° C. for 3 hours. After the treatment with dichloromethane as the extraction solvent in an ordinary manner, the obtained crude product was purified by the silica gel column chromatography to obtain the title compound.

Workup

  1. temperaturethe obtained solution was heated
  2. temperatureunder reflux for 2 hours
  3. customwas purified by the silica gel column chromatography

Sources & evidence

ORD record
ord-5f02389d24eb444f9bde626c03c502b8
Source dataset
uspto-grants-2004_11
Patent number
US06825181B1

Reaction notes

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