Methanesulfonyl chloride → N-[4-(2-tetrahydropyranyloxy)nonyl]methanesulfonamide

HRID 258597Notes

Reaction equation

HRID 258597 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH:8]([CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH2:9][CH2:10][CH2:11][NH2:12].[CH3:18][S:19](Cl)(=[O:21])=[O:20]>N1C=CC=CC=1>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH:8]([CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH2:9][CH2:10][CH2:11][NH:12][S:19]([CH3:18])(=[O:21])=[O:20]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 203276844-(2-Tetrahydropyranyloxy)nonylamine

Product 1

HCID 20327650N-[4-(2-tetrahydropyranyloxy)nonyl]methanesulfonamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred, ice cold solution of 4-(2-tetrahydropyranyloxy)nonylamine (7.29 g., 0.03 mole) in pyridine (40 ml.) is added methanesulfonylchloride (3.42 g., 0.03 mole) at such a rate as to maintain the reaction temperature at 5°-10° C. The reaction is then allowed to stand at room temperature for six hours, poured into ice water (200 ml.) and extracted with ether (2× 100 ml.). The ether is washed with ice cold 5% hydrochloric acid (2× 20 ml.), with brine (2× 25 ml.), and then dried over sodium sulfate. Evaporation in vacuo affords N-[4-(2-tetrahydropyranyloxy)nonyl]methanesulfonamide as a pale yellow liquid.

Workup

  1. temperatureto maintain the reaction temperature at 5°-10° C
  2. extractionextracted with ether (2× 100 ml.)
  3. washThe ether is washed with ice cold 5% hydrochloric acid (2× 20 ml.), with brine (2× 25 ml.)
  4. dry with materialdried over sodium sulfate
  5. customEvaporation in vacuo

Sources & evidence

ORD record
ord-41000eec5377490698155d880af27729
Source dataset
uspto-grants-1977_07
Patent number
US04033996

Reaction notes

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