Triethylamine → Ethyl-beta-methanesulfonylamino-beta-ethoxy Acrylate

HRID 1449070Notes

Reaction equation

HRID 1449070 reaction equation
[C:1]([O:5][O:6][C:7]([CH2:10][CH3:11])([NH2:9])[CH3:8])(=[O:4])[CH:2]=[CH2:3].C(N(CC)CC)C.[CH3:19][S:20](Cl)(=[O:22])=[O:21]>C1C=CC=CC=1>[C:1]([O:5][O:6][C:7]([CH2:10][CH3:11])([NH:9][S:20]([CH3:19])(=[O:22])=[O:21])[CH3:8])(=[O:4])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 86736826Ethylbeta-amino-beta-ethoxy acrylate

Product 1

HCID 86736825Ethyl-beta-methanesulfonylamino-beta-ethoxy AcrylateYield 67.5%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To a solution of 15.9 g of ethyl-β-amino-β-ethoxy acrylate in 60 ml of benzene was added 10.3 g of triethylamine, and a solution of 11.5 g of methanesulfonyl chloride in 40 ml of benzene was dropped thereinto with stirring. After the dropping, the resulting mixture was stirred at room temperature for 5 hours. The crystals formed were separated. The filtrate was concentrated under reduced pressure and the concentrated residue crystallized by cooling. When the crystals were washed with n-hexane and dried, 16 g of prismatic crystals of a melting point of 103° to 104° C. was obtained.

Workup

  1. stirringAfter the dropping, the resulting mixture was stirred at room temperature for 5 hours
  2. customThe crystals formed
  3. customwere separated
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe concentrated residue crystallized
  6. temperatureby cooling
  7. washWhen the crystals were washed with n-hexane
  8. customdried

Sources & evidence

ORD record
ord-839034f6a2784c26b0bd820fc693f70b
Source dataset
uspto-grants-1980_02
Patent number
US04188489

Reaction notes

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