Dichloromethane → HCID 66711241, compound

HRID 1261899Notes

Reaction equation

HRID 1261899 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:5]2[C:10]=1[CH:9]=[N:8][C:7]([S:11][CH3:12])=[N:6]2.C(Cl)Cl.ClC1C=CC=C(C(OO)=[O:30])C=1>>[Br:1][C:2]1[CH:3]=[C:4]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:5]2[C:10]=1[CH:9]=[N:8][C:7]([S:11]([CH3:12])=[O:30])=[N:6]2

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 70297m-Chloroperbenzoic acidHCID 66711390HCID 66711390, compound

Product 1

HCID 66711241HCID 66711241, compoundYield 86%

Procedure

Into a Round bottom flask, [A] 5-Bromo-2-methylsulfanyl-7-phenyl-pyrrolo[2,1-f][1,2,4]triazine (0.30 g, 0.00094 mol) and Methylene chloride (2 mL, 0.03 mol) were added. m-Chloroperbenzoic acid (0.178 g, 0.00103 mol) was added portion wise over 20 minutes. The reaction was stirred at room temperature for one hour. The reaction was partitioned with DCM (200 mL) and saturated NaHCO3 (200 mL). The organic was separated, washed with Brine and dried over Na2SO4. The solid was filtered and washed with DCM. The solvent was removed under vacuum to give a yellow solid. The solid was washed with hexane to give 5-Bromo-2-methanesulfinyl-7-phenyl-pyrrolo[2,1-f][1,2,4]triazine as a yellow solid (270 mg, 86%). NMR 1H (DSMO-d6)-9.24 (s, 1H), 8.24 (d, 2H, J=7.44 Hz), 7.92 (s, 1H), 7.56 (t, 2H, J=7.93 Hz), 7.47 (t, 1H, J=7.32 Hz), 2.98 (s, 3H)

Workup

  1. customThe reaction was partitioned with DCM (200 mL) and saturated NaHCO3 (200 mL)
  2. customThe organic was separated
  3. washwashed with Brine
  4. dry with materialdried over Na2SO4
  5. filtrationThe solid was filtered
  6. washwashed with DCM
  7. customThe solvent was removed under vacuum
  8. customto give a yellow solid
  9. washThe solid was washed with hexane

Sources & evidence

ORD record
ord-24dfddab36b544ac97e4087cb9d3f77b
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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