4-(1,3-Oxazol-5-yl)benzenesulphonyl chloride → 4-Oxazol-5-yl-N-[4-(1-propyl-azetidin-3-yl)-phenyl]-benzenesulfonamide

HRID 2262631Notes

Reaction equation

HRID 2262631 reaction equation
[CH2:1]([N:4]1[CH2:7][CH:6]([C:8]2[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=2)[CH2:5]1)[CH2:2][CH3:3].[O:15]1[C:19]([C:20]2[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=2)=[CH:18][N:17]=[CH:16]1>C(Cl)Cl.N1C=CC=CC=1.C(Cl)Cl>[O:15]1[C:19]([C:20]2[CH:21]=[CH:22][C:23]([S:26]([NH:14][C:11]3[CH:10]=[CH:9][C:8]([CH:6]4[CH2:5][N:4]([CH2:1][CH2:2][CH3:3])[CH2:7]4)=[CH:13][CH:12]=3)(=[O:28])=[O:27])=[CH:24][CH:25]=2)=[CH:18][N:17]=[CH:16]1

Participants

5

Reactant 2

HCID 27764154-(1,3-Oxazol-5-yl)benzenesulphonyl chlorideHCID 57470084HCID 57470084, compound

Product 1

HCID 536286704-Oxazol-5-yl-N-[4-(1-propyl-azetidin-3-yl)-phenyl]-benzenesulfonamideYield 36%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21875418Pyridine methylene chlorideSolvent

Procedure

The crude 4-(1-propyl-azetidin-3-yl)-phenylamine (40 mg, 0.21 mmol) was dissolved in CH2Cl2/pyridine 9:1 (10 ml) and 4-oxazol-5-yl-benzenesulfonyl chloride (51 mg, 0.21 mmol) was added. After stirring at room temperature for 2 h, the reaction mixture was diluted with CH2Cl2 and washed successively with 1N aqueous HCl, saturated aqueous NaHCO3 and water. The organic layer was dried over Na2SO4 and evaporated. The residue was chromatographied on silica gel (CH2Cl2:methanol, 95:5) to afford the title compound (30 mg, 36%) as a white amorphous solid.

Workup

  1. washwashed successively with 1N aqueous HCl, saturated aqueous NaHCO3 and water
  2. dry with materialThe organic layer was dried over Na2SO4
  3. customevaporated

Sources & evidence

ORD record
ord-8c00d171134740fe9479a0a7a38298f3
Source dataset
uspto-grants-2010_12
Patent number
US07851463B2

Reaction notes

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