Pyridine → 2,5-Dichloro-(2-methyl-benzooxazol-6-yl)-benzenesulfonamide

HRID 970043Notes

Reaction equation

HRID 970043 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].[N:13]1C=CC=CC=1.N[C:20]1[CH:29]=[CH:28][C:23]2[N:24]=[C:25]([CH3:27])[O:26][C:22]=2[CH:21]=1.C([O-])(O)=O.[Na+]>ClCCl>[Cl:1][C:2]1[C:7]([C:20]2[CH:29]=[CH:28][C:23]3[N:24]=[C:25]([CH3:27])[O:26][C:22]=3[CH:21]=2)=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[S:9]([NH2:13])(=[O:11])=[O:10]

Participants

6

Reactant 4

HCID 1049PyridineHCID 794012,5-Dichlorobenzenesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 5905392-Methyl-1,3-benzoxazol-6-amine

Product 1

HCID 667455202,5-Dichloro-(2-methyl-benzooxazol-6-yl)-benzenesulfonamideYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2,5-dichlorobenzenesulphonyl chloride (174 mg, 0.709 mmol) in dichloromethane (3 mL) was added pyridine (140 μL, 1.72 mmol) and the mixture was stirred under N2 for 5 min, after which time 6-amino-2-methylbenzoxazole (100 mg, 0.675 mmol) was added. The resulting mixture was stirred for 1 h at room temperature, then saturated NaHCO3 solution was added (8 mL) and the mixture was extracted into ethyl acetate (15 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 (154 mg, 64%), single spot at Rf 0.50 (60:40 hexane:ethyl acetate). mp 167.0-167.3° C., HPLC purity 97% (tR 1.97 min in 10% water-acetonitrile). 1H NMR (CDCl3): δ 7.93 (1H, d, J=2.3 Hz), 7.47 (1H, d, J=8.6 Hz), 7.46-7.40 (4H, m), 7.00 (1H, dd, J=8.6, 2.0 Hz), 2.61 (3H, s). LCMS: 355.07 (M−). FAB-MS (MH+, C14H10Cl2N2O3S): calcd 356.9867, found 356.9875.

Workup

  1. stirringThe resulting mixture was stirred for 1 h at room temperature
  2. extractionthe mixture was extracted into ethyl acetate (15 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-8a0103c87dfe43e0b34d4a50ab920b6e
Source dataset
uspto-grants-2007_12
Patent number
US07309715B2

Reaction notes

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