Chlorosulfonic acid → HCID 87295712, compound

HRID 1256082Notes

Reaction equation

HRID 1256082 reaction equation
[Cl:1][S:2]([OH:5])(=O)=[O:3].[F:6][C:7]([F:25])([F:24])[C:8]([NH:10][C:11]1[CH:12]=[C:13]([CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:14]=[CH:15][CH:16]=1)=[O:9]>C(Cl)Cl>[Cl:1][S:2]([C:14]1[CH:15]=[CH:16][C:11]([NH:10][C:8](=[O:9])[C:7]([F:25])([F:24])[F:6])=[CH:12][C:13]=1[CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])(=[O:5])=[O:3]

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acidHCID 87295564HCID 87295564, compound

Product 1

HCID 87295712HCID 87295712, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

ClSO3H (2 g, 17.3 mmol) was cooled to 0° C. and ethyl 3-(3-(2,2,2-trifluoroacetamido) phenyl)propanoate (1 g, 3.46 mmol) was added portionwise with vigorous stirring keeping the temperature below 5° C. The reaction mixture was stirred at room temperature overnight, and cautious poured onto ice. The solid produced was dissolved in CH2Cl2. The combined organic phase was washed with saturated NaHCO3 and saturated brine, dried over MgSO4 to give the product ethyl 3-(2-(chlorosulfonyl)-5-(2,2,2-trifluoroacetamido)phenyl)propanoate (0.41 g, yield 31%).

Workup

  1. customthe temperature below 5° C
  2. stirringThe reaction mixture was stirred at room temperature overnight
  3. additioncautious poured onto ice
  4. customThe solid produced
  5. washThe combined organic phase was washed with saturated NaHCO3 and saturated brine
  6. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-acad39fe74b448d3a8ac53f78a07dcc2
Source dataset
uspto-grants-2013_06
Patent number
US08461134B2

Reaction notes

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