m-Chloroperbenzoic acid → HCID 59467914, compound

HRID 1404944Notes

Reaction equation

HRID 1404944 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[S:10][CH2:11][C:12]([N:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:17][CH2:16][CH2:15]1)=[O:13].C1C=C(Cl)C=C(C(OO)=[O:32])C=1>C(Cl)Cl>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[S:10]([CH2:11][C:12]([N:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:17][CH2:16][CH2:15]1)=[O:13])=[O:32]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 684888HCID 684888, compound

Product 1

HCID 59467914HCID 59467914, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of compound 64 (167 mg, 0.49 mmol) in DCM (4 mL) cooled in a salt-ice bath was added a solution of mCPBA (77%, 110 mg, 0.49 mmol) in DCM (4 mL) drop wise. The reaction mixture was stirred for 1 hr. After diluting with DCM (30 mL), the solution washed with Na2S2O3, NaHCO3, dried over Na2SO4 and concentrated in vacuum. The crude material was purified by flash chromatography on silica gel eluting with EtOAc/hexanes (20˜50%) to give compound 65 as a white solid (164 mg, 94%). MS (APCI): m/z 357 [M+H]+. Anal. Calcd for C18H16N2O2S2: C, 60.65; H, 4.52; N, 7.86. Found: C, 60.44; H, 4.66; N, 7.73.

Workup

  1. washthe solution washed with Na2S2O3, NaHCO3
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuum
  4. customThe crude material was purified by flash chromatography on silica gel eluting with EtOAc/hexanes (20˜50%)

Sources & evidence

ORD record
ord-cb065e55e5604e8396a71a548d63c157
Source dataset
uspto-grants-2014_12
Patent number
US08916550B2

Reaction notes

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