Triethylamine → N-[1-(4-Bromo-phenyl)-cyclopropanecarbonyl]-methanesulfonamide

HRID 1512692Notes

Reaction equation

HRID 1512692 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:11]([OH:13])=O)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[CH3:18][S:19]([NH2:22])(=[O:21])=[O:20].C(N(CC)CC)C>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:11]([NH:22][S:19]([CH3:18])(=[O:21])=[O:20])=[O:13])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 72879MethanesulfonamideHCID 162279661-(4-Bromophenyl)cyclopropane-1-carboxylic acid

Product 1

HCID 66577406N-[1-(4-Bromo-phenyl)-cyclopropanecarbonyl]-methanesulfonamide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1-(4-Bromo-phenyl)-cyclopropanecarboxylic acid (5.0 g, 20.7 mmol) was dissolved in toluene (30 mL) then thionyl chloride (17.7 mL, 243 mmol) was carefully added. The reaction was heated to reflux for 4 hours then concentrated and azeotroped with toluene (2×30 mL). The intermediate acid chloride was dissolved in toluene (50 mL) then methanesulfonamide (11.41 g, 120 mmol) and triethylamine (15 mL, 0.108 mmol) were added. The reaction was refluxed for 3 hours then cooled and submitted to standard aqueous workup. The crude material was purified on silica gel to give the title compound.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 4 hours
  3. concentrationthen concentrated
  4. customazeotroped with toluene (2×30 mL)
  5. dissolutionThe intermediate acid chloride was dissolved in toluene (50 mL)
  6. temperatureThe reaction was refluxed for 3 hours
  7. temperaturethen cooled
  8. customThe crude material was purified on silica gel

Sources & evidence

ORD record
ord-dbbec30bbeba402caccb5013795b5fac
Source dataset
uspto-grants-2012_07
Patent number
US08217066B2

Reaction notes

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