Hydrochloric Acid → Ethyl 7-(methanesulfonamido)heptanoate
Reaction equation
[H-].[Na+].[CH3:3][S:4]([NH2:7])(=[O:6])=[O:5].Br[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16].Cl>CN(C)C=O.C1C=CC=CC=1>[CH3:3][S:4]([NH:7][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])(=[O:6])=[O:5]Participants
Procedure
A stirred suspension of sodium hydride (57% in mineral oil) (2.33 g., 0.055 mole) in a solvent mixture of benzene (50 ml.) and dimethylformamide (50 ml.) is treated, over 30 minutes, with methanesulfonamide (4.75 g., 0.055 mole). This mixture is heated on the steam bath for 1.5 hours, then cooled to room temperature. At this temperature is added ethyl 7-bromoheptanoate (13 g., 0.055 mole) and the reaction mixture is heated at 90° C. for 20 hours. The reaction is poured into ater (200 ml.), neutralized with hydrochloric acid and extracted with ethyl acetate (2 × 100 ml.). The ethyl acetate layer is washed with brine, dried over sodium sulfate, then concentrated in vacuo. The yield of ethyl 7-(methanesulfonamido)heptanoate is 7.1 g. (51%) boiling 165°-168°/0.1 mm.
Workup
- temperatureThis mixture is heated on the steam bath for 1.5 hours
- temperaturethe reaction mixture is heated at 90° C. for 20 hours
- additionThe reaction is poured into ater (200 ml.)
- extractionextracted with ethyl acetate (2 × 100 ml.)
- washThe ethyl acetate layer is washed with brine
- dry with materialdried over sodium sulfate
- concentrationconcentrated in vacuo
- customboiling 165°-168°
Sources & evidence
- ORD record
- ord-4c229f87bfee4431976ce88fb0c42623
- Source dataset
- uspto-grants-1976_11
- Patent number
- US03991106
Reaction notes
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