3-Chloroaniline → HCID 67338694, compound

HRID 1184535Notes

Reaction equation

HRID 1184535 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5](/[CH:13]=[CH:14]/[C:15]([OH:17])=O)[CH:6]=[CH:7][C:8]=1[S:9](=[O:12])(=[O:11])[NH2:10].S(Cl)(Cl)=O.[Cl:22][C:23]1[CH:24]=[C:25]([NH2:29])[CH:26]=[CH:27][CH:28]=1.C(N(C(C)C)CC)(C)C>C1COCC1>[Cl:22][C:23]1[CH:24]=[C:25]([NH:29][C:15](=[O:17])/[CH:14]=[CH:13]/[C:5]2[CH:6]=[CH:7][C:8]([S:9](=[O:11])(=[O:12])[NH2:10])=[C:3]([O:2][CH3:1])[CH:4]=2)[CH:26]=[CH:27][CH:28]=1

Participants

6

Reactant 4

HCID 79323-ChloroanilineHCID 24386Thionyl Chloride2×HCID 81531DiisopropylethylamineHCID 43137808HCID 43137808, compound

Product 1

HCID 67338694HCID 67338694, compoundYield 26.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of (E)-3-(3-methoxy-4-sulfamoyl-phenyl)-acrylic acid (0.291 g, 1.13 mmol) and thionyl chloride (0.100 mL, 1.36 mmol) in dry THF (15 mL) was stirred at reflux temperature for 1 h. Then a further aliquot of thionyl chloride (0.050 mL, 0.68 mmol) was added and the mixture was stirred at reflux temperature for additional 2 hrs. The mixture was then concentrated under reduced pressure, taken up with dry THF (3 mL) and added dropwise to a solution of 3-chloro-phenylamine (0.109 mL, 1.03 mmol) and diisopropylethylamine (0.705 mL, 4.12 mmol) in dry THF (13 mL). After stirring at RT for 16 hrs, the reaction mixture was concentrated under reduced pressure, taken up with DCM and washed with aqueous sodium hydrogencarbonate, and brine. The organic layer was then dried over sodium sulphate and evaporated. The resulting raw material was purified by column chromatography over silica gel (eluant DCM/acetone 9/1) to give 100 mg of the title (E)-N-(3-chloro-phenyl)-3-(3-methoxy-4-sulfamoyl-phenyl)-acrylamide as a white powder.

Workup

  1. temperatureat reflux temperature for 1 h
  2. temperatureat reflux temperature for additional 2 hrs
  3. concentrationThe mixture was then concentrated under reduced pressure
  4. stirringAfter stirring at RT for 16 hrs
  5. concentrationthe reaction mixture was concentrated under reduced pressure
  6. washwashed with aqueous sodium hydrogencarbonate, and brine
  7. dry with materialThe organic layer was then dried over sodium sulphate
  8. customevaporated
  9. customThe resulting raw material was purified by column chromatography over silica gel (eluant DCM/acetone 9/1)

Sources & evidence

ORD record
ord-2e3d4f8392ec426584b0094ac24411a9
Source dataset
uspto-grants-2014_03
Patent number
US08669261B2

Reaction notes

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