Dichloromethane → N-(2-diethylamino-ethyl)-4-(methanesulfonylamino)-2-methoxy-benzamide

HRID 32291Notes

Reaction equation

HRID 32291 reaction equation
[CH2:1]([N:3]([CH2:26][CH3:27])[CH2:4][CH2:5][NH:6][C:7](=[O:25])[C:8]1[CH:13]=[CH:12][C:11]([N:14](S(C)(=O)=O)[S:15]([CH3:18])(=[O:17])=[O:16])=[CH:10][C:9]=1[O:23][CH3:24])[CH3:2].[OH-].[K+].C(=O)(O)[O-].[Na+].C(Cl)Cl>O1CCCC1>[CH2:26]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][NH:6][C:7](=[O:25])[C:8]1[CH:13]=[CH:12][C:11]([NH:14][S:15]([CH3:18])(=[O:16])=[O:17])=[CH:10][C:9]=1[O:23][CH3:24])[CH3:27]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 14797Potassium HydroxideHCID 516892Sodium BicarbonateHCID 66934940N-(2-diethylamino-ethyl)-4-(bismethanesulfonylamino)-2-methoxy-benzamide

Product 1

HCID 16748090N-(2-diethylamino-ethyl)-4-(methanesulfonylamino)-2-methoxy-benzamideYield 92.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

150 mg (0.36 mmol) of N-(2-diethylamino-ethyl)-4-(bismethanesulfonylamino)-2-methoxy-benzamide is dissolved in 10 ml of tetrahydrofuran and mixed with 1 ml of 1N potassium hydroxide solution. It is stirred for 2 hours at room temperature. Then, the tetrahydrofuran is drawn off in a vacuum, mixed with 25 ml of saturated sodium bicarbonate solution and shaken out three times with 25 ml each of methylene chloride. The collected organic phase is dried, filtered and concentrated by evaporation, and 114 mg (91.9% of theory) of N-(2-diethylamino-ethyl)-4-(methanesulfonylamino)-2-methoxy-benzamide is obtained.

Workup

  1. customThe collected organic phase is dried
  2. filtrationfiltered
  3. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-678bca9214434652ade6c26edceda413
Source dataset
uspto-grants-2008_09
Patent number
US07427390B2

Reaction notes

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