Ethyl Acetate → HCID 7235814, compound

HRID 2172692Notes

Reaction equation

HRID 2172692 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([S:9](Cl)(=[O:11])=[O:10])=[CH:5][CH:4]=1)#[N:2].C(O[CH2:17][CH3:18])(=O)C>N1C=CC=CC=1.O>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([S:9]([NH:2][C:1]2[CH:3]=[CH:4][CH:5]=[CH:6][C:17]=2[CH3:18])(=[O:11])=[O:10])=[CH:5][CH:4]=1)#[N:2]

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 394974-Cyanobenzenesulfonyl chloride

Product 1

HCID 7235814HCID 7235814, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

O-toluidine (Fluka; 0.118 mL, 1.1 mmol) was added to a clear light yellow solution of 4-cyano-benzenesulfonyl chloride (ABCR GmbH & Co. KG; 202 mg, 1 mmol) in pyridine (5 mL). The resulting clear red-brown solution was then stirred at room temperature for 18 hrs. Subsequently the reaction mixture was diluted with water (50 mL) and ethyl acetate (50 mL). The liquid layers were separated and the aqueous fraction was re-extracted twice with ethyl acetate (25 mL). The combined organic layers were washed with 0.1 M hydrochloric acid and brine (50 mL each), dried with sodium sulfate, filtered and evaporated under reduced pressure. The residue was dried under high vacuum to give 4-cyano-N-o-tolyl-benzenesulfonamide (314 mg, 0.92 mmol, 92% yield) as pale brown oil.

Workup

  1. customThe liquid layers were separated
  2. extractionthe aqueous fraction was re-extracted twice with ethyl acetate (25 mL)
  3. washThe combined organic layers were washed with 0.1 M hydrochloric acid and brine (50 mL each)
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe residue was dried under high vacuum

Sources & evidence

ORD record
ord-f9999a328d134933aa12b986a2f8ffd4
Source dataset
uspto-grants-2015_06
Patent number
US09056843B2

Reaction notes

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