Benzene → HCID 58107521, compound

HRID 873691Notes

Reaction equation

HRID 873691 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][C:3]=1[S:11](=[O:14])(=[O:13])[NH2:12].[Cl-].[Al+3].[Cl-].[Cl-].[CH:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.Cl>C(Cl)Cl>[C:6]([C:5]1[CH:9]=[CH:10][C:2]([Cl:1])=[C:3]([S:11]([NH2:12])(=[O:14])=[O:13])[CH:4]=1)(=[O:7])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 241BenzeneHCID 313Hydrochloric AcidHCID 30179793-(Aminosulfonyl)-4-chlorobenzoyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 58107521HCID 58107521, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a well stirred solution of 4-chloro-3-sulfamoyl-benzoyl chloride (0.5 g, 1.97 mmol) in 5 mL methylene chloride is added aluminum chloride (0.485 g, 1.85 mmol). After 30 min, benzene (1 mL, 5.72 mmol) is added and the reaction is stirred for 2 h at room temperature. The reaction mixture is then poured over ice, acidified with 6 N HCl and extracted three times with diethyl ether. The organic layers were combined, dried with magnesium sulfate, filtered and concentrated in vacuo. The resulting residue is purified via silica gel chromatography to yield 40 mg (69%) of the title compound as a tan solid. MS (m/z): 294 (M-1). Analytics calculated for C13H10ClNO3S: C, 52.8; H, 3.41; N, 4.74. Found: C, 52.62; H, 3.21; N, 4.72.

Workup

  1. additionThe reaction mixture is then poured over ice
  2. extractionextracted three times with diethyl ether
  3. dry with materialdried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue is purified via silica gel chromatography

Sources & evidence

ORD record
ord-80e9a0fc96a348909c8b031affe3f5fa
Source dataset
uspto-grants-2015_03
Patent number
US08975439B2

Reaction notes

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