Methanesulfonyl chloride → HCID 68842701, compound

HRID 1784873Notes

Reaction equation

HRID 1784873 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:11]=[C:12]([NH2:17])[CH:13]=[C:14]([Br:16])[CH:15]=1.[CH3:18][S:19](Cl)(=[O:21])=[O:20]>N1C=CC=CC=1.CN(C1C=CN=CC=1)C>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:11]=[C:12]([NH:17][S:19]([CH3:18])(=[O:21])=[O:20])[CH:13]=[C:14]([Br:16])[CH:15]=1

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 68843465HCID 68843465, compound

Product 1

HCID 68842701HCID 68842701, compoundYield 55.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

To a solution of 3-benzoxazol-2-yl-5-bromo-phenylamine (0.12 g, 0.42 mmol) in pyridine (2.0 mL) at room temperature was added methanesulfonyl chloride (0.14 g, 1.30 mmol) and catalytic DMAP. The resulting mixture was stirred at room temperature for 17 hours. The solvent was removed under vacuum and the residue was purified by preparative TLC eluting with 4:1/hexanes:ethyl acetate to give N-(3-benzoxazol-2-yl-5-bromo-phenyl)-methanesulfonamide (85.0 mg, 55%) as a yellow solid.

Workup

  1. customThe solvent was removed under vacuum
  2. customthe residue was purified by preparative TLC
  3. washeluting with 4:1/hexanes

Sources & evidence

ORD record
ord-381c471eddfe4b3a8622d9272982483c
Source dataset
uspto-grants-2009_03
Patent number
US07504401B2

Reaction notes

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