Hydrochloric Acid → N-(2-Hydroxycyclohexyl)methanesulfonamide

HRID 1181162Notes

Reaction equation

HRID 1181162 reaction equation
[O:1]1[CH:3]2[CH2:4][CH2:5][CH2:6][CH2:7][CH:2]12.[CH3:8][S:9]([NH2:12])(=[O:11])=[O:10].C(O[K])(C)(C)C.Cl>O1CCCC1>[CH3:8][S:9]([NH:12][CH:3]1[CH2:4][CH2:5][CH2:6][CH2:7][CH:2]1[OH:1])(=[O:11])=[O:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 9246Cyclohexene oxideHCID 72879MethanesulfonamideHCID 178418922HCID 178418922, compound

Product 1

HCID 57747886N-(2-Hydroxycyclohexyl)methanesulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a nitrogen atmosphere, a mixture of 108 g of 1,2-epoxycyclohexane, 95.1 g of methanesulfonamide, 11.2 g of t-butoxypotassium, and 1,000 g of tetrahydrofuran was heated under reflux for 100 hours. The reaction solution was neutralized with hydrochloric acid and then subjected to conventional aqueous work-up. Purification by column chromatography yielded an alcohol compound, 2-[(methylsulfonyl)amino]cyclohexanol. In a nitrogen atmosphere, the alcohol compound was combined with 111 g of triethylamine and 2,000 g of acetonitrile, to which 105 g of methacryloyl chloride was added dropwise at −20° C. The mixture was gradually warmed to room temperature and then stirred for 10 hours. The reaction mixture was subjected to conventional aqueous work-up and purified by column chromatography, obtaining 165 g of 2-[(methylsulfonyl)amino]-cyclohexyl methacrylate. The yield was 63% based on the methanesulfonamide.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 100 hours
  3. customPurification by column chromatography

Sources & evidence

ORD record
ord-23c9c3e7236b422f9eed3f59573af91a
Source dataset
uspto-grants-2007_10
Patent number
US07285368B2

Reaction notes

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