Cyclopropylamine → 2-(Trimethylsilyl)ethyl 3-(cyclopropylsulfamoyl)benzoate

HRID 1025425Notes

Reaction equation

HRID 1025425 reaction equation
Cl[S:2]([C:5]1[CH:6]=[C:7]([CH:17]=[CH:18][CH:19]=1)[C:8]([O:10][CH2:11][CH2:12][Si:13]([CH3:16])([CH3:15])[CH3:14])=[O:9])(=[O:4])=[O:3].[CH:20]1([NH2:23])[CH2:22][CH2:21]1>N1C=CC=CC=1>[CH:20]1([NH:23][S:2]([C:5]2[CH:6]=[C:7]([CH:17]=[CH:18][CH:19]=2)[C:8]([O:10][CH2:11][CH2:12][Si:13]([CH3:16])([CH3:15])[CH3:14])=[O:9])(=[O:4])=[O:3])[CH2:22][CH2:21]1

Participants

4

Reactant 2

HCID 69828CyclopropylamineHCID 866763342-(Trimethylsilyl)ethyl 3-(chlorosulfonyl)benzoate

Product 1

HCID 712384462-(Trimethylsilyl)ethyl 3-(cyclopropylsulfamoyl)benzoate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 2.00 g of 2-(trimethylsilyl)ethyl 3-(chlorosulfonyl)benzoate, 1.2 mL of cyclopropylamine, and 20 mL of pyridine was stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure, and to the residue was added an aqueous citric acid solution, followed by extraction with ethyl acetate. The organic layer was washed with 1.0 M hydrochloric acid and saturated brine in this order, then dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain 2.12 g of 2-(trimethylsilyl)ethyl 3-(cyclopropylsulfamoyl)benzoate as a pale yellow oily substance. EI: 341

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionto the residue was added an aqueous citric acid solution
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with 1.0 M hydrochloric acid and saturated brine in this order
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ae01795146524e578c6a8793948035df
Source dataset
uspto-grants-2014_05
Patent number
US08729068B2

Reaction notes

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