Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1) | HCID 77210 | — |
| Reactant | HCID 86679550 | HCID 86679550 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 86679549 | HCID 86679549 | 104.7% |
Reaction Steps
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.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09265768B2 |
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| Source dataset | uspto-grants-2016_02 |
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| ORD ID | ord-50ec94e494e047c9992edb4b42a3e2c0 |
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| Source note | uspto-grants-2016_02 |
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