m-Chloroperbenzoic acid → 4-(7-bromo-benzooxazol-2-ylamino)-2,N,N-trimethyl-benzamide

HRID 469821Notes

Reaction equation

HRID 469821 reaction equation
[Br:1][C:2]1[C:10]2[O:9][C:8](SC)=[N:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=O)C=1.[NH2:24][C:25]1[CH:35]=[CH:34][C:28]([C:29]([N:31]([CH3:33])[CH3:32])=[O:30])=[C:27]([CH3:36])[CH:26]=1>ClCCl>[Br:1][C:2]1[C:10]2[O:9][C:8]([NH:24][C:25]3[CH:35]=[CH:34][C:28]([C:29]([N:31]([CH3:33])[CH3:32])=[O:30])=[C:27]([CH3:36])[CH:26]=3)=[N:7][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 536229124-amino-N,N,2-trimethylbenzamideHCID 674568117-Bromo-2-(methylthio)benzo[d]oxazole

Product 1

HCID 674578214-(7-bromo-benzooxazol-2-ylamino)-2,N,N-trimethyl-benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.49 g (2.01 mmol) 7-bromo-2-methylsulfanyl-benzooxazole in 30 ml dichloromethane, 3-chloroperbenzoic acid (0.494 g, 2.01 mmol) is added. This mixture is stirred for 1 h at room temperature. Then, 0.325 g (1.82 mmol) 4-amino-2,N,N-trimethyl-benzamide is added and the reaction mixture is heated to 40° C. with stirring continued for 20 h. The reaction mixture is concentrated in vacuo and the residue is purified by chromatography (silicagel, hexane:EtOAc=1:1=>1:4) to afford the title compound as an off-white crystalline solid.

Workup

  1. temperaturethe reaction mixture is heated to 40° C.
  2. stirringwith stirring
  3. waitcontinued for 20 h
  4. concentrationThe reaction mixture is concentrated in vacuo
  5. customthe residue is purified by chromatography (silicagel, hexane:EtOAc=1:1=>1:4)

Sources & evidence

ORD record
ord-5106ed6459f947d7a9e5871c155eacf2
Source dataset
uspto-grants-2014_01
Patent number
US08629168B2

Reaction notes

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