Pyridine → HCID 11256388, compound

HRID 1766304Notes

Reaction equation

HRID 1766304 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[S:9](Cl)(=[O:11])=[O:10].N1C=CC=CC=1.[NH2:19][C:20]1[CH:21]=[CH:22][C:23]2[O:27][N:26]=[CH:25][C:24]=2[CH:28]=1.C([O-])(O)=O.[Na+]>ClCCl>[O:27]1[C:23]2[CH:22]=[CH:21][C:20]([NH:19][S:9]([C:3]3[CH:4]=[C:5]([Cl:8])[CH:6]=[CH:7][C:2]=3[Cl:1])(=[O:11])=[O:10])=[CH:28][C:24]=2[CH:25]=[N:26]1

Participants

6

Reactant 4

HCID 1049PyridineHCID 794012,5-Dichlorobenzenesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 183734211,2-Benzoxazol-5-amine

Product 1

HCID 11256388HCID 11256388, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2,5-dichlorobenzenesulphonyl chloride (192 mg, 0.783 mmol), in dichloromethane (4 mL) was added pyridine (150 μL, 1.86 mmol) and the mixture was stirred under N2 for 5 min, after which time 5-amino-1,2-benzisoxazole (100 mg, 0.746 mmol) was added. The resulting mixture was stirred for 2 h at room temperature, then saturated NaHCO3 solution (10 mL) was added and the mixture was extracted into ethyl acetate (20 mL). The organic phase was washed with brine, dried (Na2SO4), filtered and evaporated to give a residue that was purified using flash chromatography to afford a white solid (174 mg, 68%), single spot at Rf 0.68 (1:1 hexane:ethyl acetate). mp 172.9-173.6° C., HPLC purity 99+% (tR 2.41 min in 10% water-acetonitrile). 1H NMR (CDCl3): δ 8.64 (1H, s), 7.89 (1H, d, J=2.2 Hz), 7.56-7.28 (5H, m). LCMS: 341.07 (M−). FAB-MS (MH+, C13H8Cl2N2O3S): calcd 342.9711, found 342.9710.

Workup

  1. stirringThe resulting mixture was stirred for 2 h at room temperature
  2. extractionthe mixture was extracted into ethyl acetate (20 mL)
  3. washThe organic phase was washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customto give a residue that
  8. customwas purified

Sources & evidence

ORD record
ord-623a41dd555c47edaef35499367e593f
Source dataset
uspto-grants-2007_06
Patent number
US07230020B2

Reaction notes

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