Water → HCID 20681420, compound

HRID 651692Notes

Reaction equation

HRID 651692 reaction equation
[CH3:1][NH:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl[S:11]([CH2:14][C:15]([O:17][CH3:18])=[O:16])(=[O:13])=[O:12].O>ClCCl>[CH2:3]([N:2]([CH3:1])[S:11]([CH2:14][C:15]([O:17][CH3:18])=[O:16])(=[O:13])=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 962WaterHCID 7669N-MethylbenzylamineHCID 11435213Methyl (chlorosulfonyl)acetate

Product 1

HCID 20681420HCID 20681420, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of N-methyl benzylamine (7 ml, 54.2 mmol) in dichloromethane (10 ml) at 0-5° C. under an atmosphere of nitrogen was added dropwise a solution of methyl chlorosulfonylacetate (prepared by the method of M. J. Szymonifka and J. V. Heck, Tetrahedron Lett., 1989, 30, 22, 2869) (4.26 g, 24.7 mmol) in dichloromethane (5 ml), maintaining the temperature below 5° C. The yellow solution was then warmed to ambient temperature over a 2 hr period before water (30 ml) was added. The organic phase was partitioned and evaporated in vacuo to give a yellow oil. This was purified by flash column chromatography (diethyl ether:hexane 1:1 as eluant) to give the subtitle compound (3.9 g, 61%) as a colourless oil.

Workup

  1. customprepared by the method of M
  2. additionwas added
  3. customThe organic phase was partitioned
  4. customevaporated in vacuo
  5. customto give a yellow oil
  6. customThis was purified by flash column chromatography (diethyl ether:hexane 1:1 as eluant)

Sources & evidence

ORD record
ord-4b9c6d231a4c4397bb12517956aae3cd
Source dataset
uspto-grants-2001_08
Patent number
US06281357B1

Reaction notes

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