4-(1,3-Oxazol-5-yl)benzenesulphonyl chloride → HCID 59577086, compound

HRID 2041966Notes

Reaction equation

HRID 2041966 reaction equation
[O:1]1[C:5]([C:6]2[CH:11]=[CH:10][C:9]([S:12](Cl)(=[O:14])=[O:13])=[CH:8][CH:7]=2)=[CH:4][N:3]=[CH:2]1.O.[NH3:17]>O1CCCC1>[O:1]1[C:5]([C:6]2[CH:11]=[CH:10][C:9]([S:12]([NH2:17])(=[O:14])=[O:13])=[CH:8][CH:7]=2)=[CH:4][N:3]=[CH:2]1

Participants

4

Reactant 2

HCID 27764154-(1,3-Oxazol-5-yl)benzenesulphonyl chlorideHCID 12896473Azane;hydrate

Product 1

HCID 59577086HCID 59577086, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 4-(1,3-oxazol-5-yl)benzenesulfonyl chloride (1.00 g, 4.10 mmol) in tetrahydrofuran (15.0 mL) was added 25% ammonia water solution (5.00 mL) at room temperature. After 1 h the reaction mixture was partitioned between ethyl acetate (100.0 mL) and 1.0 N hydrochloric acid (10.0 mL) and separated. The organic layer was washed with water (2×40 mL), saturated sodium chloride (80 mL), dried (MgSO4), filtered. The filtrate was concentrated under reduced pressure to provide 4-(1,3-oxazol-5-yl)benzenesulfonamide (800 mg, 87%) as a solid.

Workup

  1. customAfter 1 h the reaction mixture was partitioned between ethyl acetate (100.0 mL) and 1.0 N hydrochloric acid (10.0 mL)
  2. customseparated
  3. washThe organic layer was washed with water (2×40 mL), saturated sodium chloride (80 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-a28aad63a6414442bf5b67ddc5d3a7d7
Source dataset
uspto-grants-2013_11
Patent number
US08586571B2

Reaction notes

Loading…