Methanesulfonyl chloride → N-[4-[2-[(3,4,5-Trimethoxyphenyl)amino]-7-benzoxazolyl]phenyl]methanesulfonamide

HRID 469805Notes

Reaction equation

HRID 469805 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[O:15][C:14]([NH:17][C:18]4[CH:23]=[C:22]([O:24][CH3:25])[C:21]([O:26][CH3:27])=[C:20]([O:28][CH3:29])[CH:19]=4)=[N:13][C:12]=3[CH:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[CH3:30][S:31](Cl)(=[O:33])=[O:32]>N1C=CC=CC=1>[CH3:29][O:28][C:20]1[CH:19]=[C:18]([NH:17][C:14]2[O:15][C:16]3[C:8]([C:5]4[CH:6]=[CH:7][C:2]([NH:1][S:31]([CH3:30])(=[O:33])=[O:32])=[CH:3][CH:4]=4)=[CH:9][CH:10]=[CH:11][C:12]=3[N:13]=2)[CH:23]=[C:22]([O:24][CH3:25])[C:21]=1[O:26][CH3:27]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 24800772HCID 24800772, compound

Product 1

HCID 24801129N-[4-[2-[(3,4,5-Trimethoxyphenyl)amino]-7-benzoxazolyl]phenyl]methanesulfonamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 0.12 g (0.307 mmol) [7-(4-amino-phenyl)-benzooxazol-2-yl]-(3,4,5-trimethoxy-phenyl)-amine (example 11) and 0.041 g (0.36 mmol) methanesulfonyl chloride in 6 ml pyridine is stirred for 1.5 h at room temperature. Then the reaction mixture is poured on water and extracted 3× with EtOAc. The combined organic layers are washed with 0.1N NaOH solution and water, dried over MgSO4, filtered and the filtrate is concentrated in vacuo. The residue is purified by crystallisation from dichloromethane/diethyl ether to afford the title compound as off-white crystals. Rt=2.22 min (Waters Symmetry C8, 2.1×50 mm, detection 210-250 nM, 5% to 100% CH3CN in H2O in 2 min+0.05% TFA, flow rate 1.0 ml/min); MS: 470 (M+1)+; m.p. 222-225° C.

Workup

  1. additionThen the reaction mixture is poured on water
  2. extractionextracted 3× with EtOAc
  3. washThe combined organic layers are washed with 0.1N NaOH solution and water
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationthe filtrate is concentrated in vacuo
  7. customThe residue is purified by crystallisation from dichloromethane/diethyl ether

Sources & evidence

ORD record
ord-2b03cf05c2354c3ea76ac9aa90c389fa
Source dataset
uspto-grants-2014_01
Patent number
US08629168B2

Reaction notes

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