m-Chloroperbenzoic acid → HCID 66711591, compound

HRID 1262121Notes

Reaction equation

HRID 1262121 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[C:11]1[N:19]2[C:14]([CH:15]=[N:16][C:17]([S:20][CH3:21])=[N:18]2)=[CH:13][CH:12]=1.ClC1C=C(C=CC=1)C(OO)=[O:27]>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[C:11]1[N:19]2[C:14]([CH:15]=[N:16][C:17]([S:20]([CH3:21])=[O:27])=[N:18]2)=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 66711556HCID 66711556, compound

Product 1

HCID 66711591HCID 66711591, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

7-(2,4-Dimethoxy-phenyl)-2-methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazine (592 mg, 1.00 equiv) and m-chloroperoxybenzoic acid (77%, 462 mg, 1.05 equiv) were dissolved in methylene chloride and stirred for 2 hours at room temperature. Partitioned between methylene chloride and saturated aqueous sodium bicarbonate. Dried over magnesium sulfate. Triturated with ether to afford 7-(2,4-dimethoxy-phenyl)-2-methanesulfinyl-pyrrolo[2,1-f][1,2,4]triazine as a yellow solid, 605 mg. LCMS (E/I+) 318 (M+H). NMR 1H (CDCl3) 9.02 (s, 1H), 7.22-7.34 (m, 2H), 7.03 (s, 1H), 6.67-6.77 (m, 2H), 3.93 (s, 3H), 3.86 (s, 3H), 3.02 (s, 3H).

Workup

  1. customPartitioned between methylene chloride and saturated aqueous sodium bicarbonate
  2. dry with materialDried over magnesium sulfate
  3. customTriturated with ether

Sources & evidence

ORD record
ord-05b73c9b2a31458ab98d5070cb8f6c0e
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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