Triethylamine → 4-[(Methanesulfonyl)amino]cyclohexyl 2-methylprop-2-enoate

HRID 1181164Notes

Reaction equation

HRID 1181164 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[NH2:6][CH:7]1[CH2:12][CH2:11][CH:10]([OH:13])[CH2:9][CH2:8]1.C(N(CC)CC)C.[C:21](Cl)(=[O:25])[C:22]([CH3:24])=[CH2:23]>CN(C)C=O>[C:21]([O:13][CH:10]1[CH2:11][CH2:12][CH:7]([NH:6][S:2]([CH3:1])(=[O:4])=[O:3])[CH2:8][CH2:9]1)(=[O:25])[C:22]([CH3:24])=[CH2:23]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 13528Methacryloyl chlorideHCID 31297Methanesulfonyl chlorideHCID 812934-Aminocyclohexanol

Product 1

HCID 589805034-[(Methanesulfonyl)amino]cyclohexyl 2-methylprop-2-enoateYield 75.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a nitrogen atmosphere, 115 g of methanesulfonyl chloride was added dropwise to a mixture of 115 g of 4-aminocyclohexanol, 212 g of triethylamine and 1,000 g of N,N-dimethylformamide at −20° C. The mixture was stirred for one hour, after which 105 g of methacryloyl chloride was added dropwise at −20° C. The mixture was gradually warmed to room temperature and then stirred for 5 hours. The reaction mixture was subjected to conventional aqueous work-up and purified by column chromatography, obtaining 196 g of 4-[(methylsulfonyl)amino]cyclohexyl methacrylate. The yield was 75% based on the 4-aminocyclohexanol.

Workup

  1. stirringstirred for 5 hours
  2. custompurified by column chromatography

Sources & evidence

ORD record
ord-8342ef583487450dbae0e7586a302a45
Source dataset
uspto-grants-2007_10
Patent number
US07285368B2

Reaction notes

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