Hydrochloric Acid → Ethyl 7-(methanesulfonamido)heptanoate

HRID 258598Notes

Reaction equation

HRID 258598 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>O.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

8

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 72879MethanesulfonamideHCID 122490Ethyl 7-bromoheptanoate

Product 1

HCID 12150839Ethyl 7-(methanesulfonamido)heptanoate

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A stirred suspension of sodium hydride (57%) (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 is heated at 90° C. for twenty hours. The reaction is poured into water (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

  1. temperatureThis mixture is heated on the steam bath for 1.5 hours
  2. temperaturethe reaction is heated at 90° C. for twenty hours
  3. extractionextracted with ethyl acetate (2× 100 ml.)
  4. washThe ethyl acetate layer is washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customboiling 165°-168°

Sources & evidence

ORD record
ord-c1b9952190154832a4fdb7f2e99115bd
Source dataset
uspto-grants-1977_07
Patent number
US04033996

Reaction notes

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