Methyl bromoacetate → Methyl 2-(5-((2,4,6-trimethoxystyrylsulfonyl)methyl)-2-methoxyphenylamino)acetate

HRID 1183212Notes

Reaction equation

HRID 1183212 reaction equation
Br[CH2:2][C:3]([O:5][CH3:6])=[O:4].C([O-])(=O)C.[Na+].[CH3:12][O:13][C:14]1[CH:34]=[C:33]([O:35][CH3:36])[CH:32]=[C:31]([O:37][CH3:38])[C:15]=1/[CH:16]=[CH:17]/[S:18]([CH2:21][C:22]1[CH:23]=[CH:24][C:25]([O:29][CH3:30])=[C:26]([NH2:28])[CH:27]=1)(=[O:20])=[O:19]>CO>[CH3:12][O:13][C:14]1[CH:34]=[C:33]([O:35][CH3:36])[CH:32]=[C:31]([O:37][CH3:38])[C:15]=1[CH:16]=[CH:17][S:18]([CH2:21][C:22]1[CH:23]=[CH:24][C:25]([O:29][CH3:30])=[C:26]([NH:28][CH2:2][C:3]([O:5][CH3:6])=[O:4])[CH:27]=1)(=[O:20])=[O:19]

Participants

5

Reactant 3

HCID 60984Methyl bromoacetateHCID 517045Sodium AcetateHCID 11486204(E)-2-methoxy-5-(((2,4,6-trimethoxystyryl)sulfonyl)methyl)aniline

Product 1

HCID 76144830Methyl 2-(5-((2,4,6-trimethoxystyrylsulfonyl)methyl)-2-methoxyphenylamino)acetateYield 85%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of methyl bromoacetate (5 mmol) and sodium acetate (5 mmol) in methanol (20 mL) was added (E)-5-((2,4,6-trimethoxystyrylsulfonyl)methyl)-2-methoxybenzenamine (1 mmol). The resulting mixture was heated to reflux temperature. The heated mixture was stirred at reflux temperature for 12 to 15 h. The heated mixture was then cooled and poured onto water ice (about 100 g). A precipitate formed. The precipitate was separated by filtration to provide the product in 85% yield. m.p. 182-185° C.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux temperature
  3. temperatureat reflux temperature for 12 to 15 h
  4. temperatureThe heated mixture was then cooled
  5. additionpoured onto water ice (about 100 g)
  6. customA precipitate formed
  7. customThe precipitate was separated by filtration
  8. customto provide the product in 85% yield

Sources & evidence

ORD record
ord-2058176c7c3a4be08e7dbc1cc8763d4b
Source dataset
uspto-grants-2014_03
Patent number
US08664272B2

Reaction notes

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