Triethylamine → HCID 21704949, compound

HRID 1595508Notes

Reaction equation

HRID 1595508 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[OH:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([N:15](C)[C:16]([NH2:18])=[O:17])=[CH:11][CH:10]=1.[CH2:20](N(CC)CC)C>ClCCl>[CH3:1][S:2]([O:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]([NH:18][CH3:20])=[O:17])=[CH:11][CH:10]=1)(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 54559364HCID 54559364, compound

Product 1

HCID 21704949HCID 21704949, compoundYield 31.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

47 g (0.412 mole) methanesulfonyl chloride in dichloromethane was added in small portions to a solution of 20 g (0.103 mole) N-[4-(2-hydroxyethyl)phenyl]-N1-methylurea and 41.7 g (0.412 mole) triethylamine in 500 ml dichloromethane at 0° C. After stirring at room temperature over night the reaction mixture was washed with 2 M hydrochloric acid and sodium bicarbonate. The organic phase was dried and concentrated by evaporation in vacuo and the formed precipitate was collected by filtration to give 8.81 g (yield 31%) of 4-(methylaminocarbonylamino)phenethyl methanesulfonate.

Workup

  1. washwas washed with 2 M hydrochloric acid and sodium bicarbonate
  2. customThe organic phase was dried
  3. concentrationconcentrated by evaporation in vacuo
  4. filtrationthe formed precipitate was collected by filtration

Sources & evidence

ORD record
ord-59873dcaf6724a8aba6d3c3b1b032b16
Source dataset
uspto-grants-2001_09
Patent number
US06288096B1

Reaction notes

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