Water → HCID 86679549, compound

HRID 1776597Notes

Reaction equation

HRID 1776597 reaction equation
[CH3:1][O:2][C:3]1[CH:13]=[CH:12][C:6]([C:7]([O:9][CH2:10]C)=[O:8])=[CH:5][C:4]=1[NH:14][S:15]([CH3:18])(=[O:17])=[O:16].Cl.Cl[CH2:21][CH2:22][N:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:13]=[CH:12][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][C:4]=1[N:14]([CH2:21][CH2:22][N:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1)[S:15]([CH3:18])(=[O:17])=[O:16]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)HCID 86679550HCID 86679550, compound

Product 1

HCID 86679549HCID 86679549, compoundYield 104.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of ethyl 4-methoxy-3-(methylsulfonamido)benzoate (0.600 g, 2.314 mmol) in dry DMF (23 ml), 4-(2-chloroethyl)morpholine hydrochloride (0.517 g, 2.78 mmol) and K2CO3 (0.704 g, 5.09 mmol) were sequentially added stirring at RT under nitrogen, and the reaction was heated at 70° C. overnight. Water (40 ml) was added, and the mixture was extracted Et2O (3×) and then with EtOAc (3×). The combined organic layers were dried over Na2SO4, and the solvent was removed. The crude was purified by flash chromatography on silica gel column (EtOAc:MeOH=97:3) affording methyl 4-methoxy-3-(N-(2-morpholinoethyl)methylsulfonamido)-benzoate (0.902 g, yield supposed to be quantitative, MS/ESI+ 373.0 [MH]+). This crude was used as such, without any further purification.

Workup

  1. temperaturethe reaction was heated at 70° C. overnight
  2. extractionthe mixture was extracted Et2O (3×)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. customthe solvent was removed
  5. customThe crude was purified by flash chromatography on silica gel column (EtOAc:MeOH=97:3)

Sources & evidence

ORD record
ord-50ec94e494e047c9992edb4b42a3e2c0
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

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