Dichloromethane → HCID 66710941, compound

HRID 1261923Notes

Reaction equation

HRID 1261923 reaction equation
ClC1C=CC(OC)=C(C2N3C(C=NC(SC)=N3)=CC=2)C=1.[Cl:21][C:22]1[CH:23]=[CH:24][C:25]([O:40][CH3:41])=[C:26]([C:28]2[N:36]3[C:31]([CH:32]=[N:33][C:34]([S:37]([CH3:39])=[O:38])=[N:35]3)=[CH:30][CH:29]=2)[CH:27]=1.C(Cl)Cl.ClC1C=CC=C(C(OO)=O)C=1>>[Cl:21][C:22]1[CH:23]=[CH:24][C:25]([O:40][CH3:41])=[C:26]([C:28]2[N:36]3[C:31]([CH:32]=[N:33][C:34]([S:37]([CH3:39])=[O:38])=[N:35]3)=[CH:30][CH:29]=2)[CH:27]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 70297m-Chloroperbenzoic acidHCID 66710940HCID 66710940, compound

Product 1

HCID 66710941HCID 66710941, compoundYield 91%

Procedure

7-(5-Chloro-2-methoxy-phenyl)-2-methanesulfinyl-pyrrolo[2,1-f][1,2,4]triazine 7-(5-Chloro-2-methoxy-phenyl)-2-methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazine (0.730 g, 0.00239 mol) was dissolved in Methylene chloride (20 mL, 0.4 mol) and the mixture was treated with m-Chloroperbenzoic acid (0.556 g, 0.00322 mol). The reaction was allowed to stir at room temperature until HPLC showed consumption of starting material. The reaction was partitioned between sodium thiosulfate and DCM and the combined organic layers were dried over saturated sodium sulfate. The solution was filtered and reduced. The solid was then triturated with ether to afford 700 mg of 7-(5-Chloro-2-methoxy-phenyl)-2-methanesulfinyl-pyrrolo[2,1-f][1,2,4]triazine as a yellow powder. (M+H)=322.6.

Workup

  1. customconsumption of starting material
  2. customThe reaction was partitioned between sodium thiosulfate and DCM
  3. dry with materialthe combined organic layers were dried over saturated sodium sulfate
  4. filtrationThe solution was filtered
  5. customThe solid was then triturated with ether

Sources & evidence

ORD record
ord-0f204b6e6dfd47809d790d85b292a4b8
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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