Sodium Thiosulfate → HCID 59472239, compound

HRID 78618Notes

Reaction equation

HRID 78618 reaction equation
C(S[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[N:12]=[C:13]([C:18]2[O:19][C:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[N:21][N:22]=2)[C:14]([NH2:17])=[N:15][CH:16]=1)(C)C.Cl[C:30]1[CH:31]=C(C(OO)=O)C=C[CH:35]=1.[S:40]([O-:44])([O-])(=[O:42])=S.[Na+].[Na+].C(=O)(O)[O-].[Na+]>ClCCl>[CH:30]([S:40]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[N:12]=[C:13]([C:18]2[O:19][C:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[N:21][N:22]=2)[C:14]([NH2:17])=[N:15][CH:16]=1)(=[O:44])=[O:42])([CH3:31])[CH3:35]

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 59472054HCID 59472054, compound

Product 1

HCID 59472239HCID 59472239, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-(2-isopropylsulfanylphenyl)-3-(5-phenyl-1,3,4-oxadiazol-2-yl)pyrazin-2-amine (40 mg, 0.1027 mmol) was dissolved in dichloromethane (10 mL) followed by the portionwise addition of 3-chlorobenzenecarboperoxoic acid (70.89 mg, 0.4108 mmol) over 10 min. The resulting mixture was stirred at room temperature for 2 h, and poured onto a 50/50 mixture of saturated aqueous sodium thiosulfate solution and saturated aqueous sodium bicarbonate solution (20 mL). The layers were separated and the organic layer was washed with dilute NaHCO3 solution (1×10 mL) and brine (1×10 mL) and then concentrated in vacuo to leave a solid. The solid was purified by column chromatography on silica eluting with 50% ether/petroleum ether to afford the product as a yellow solid. (20.25 mg, 36% yield); 1H NMR (400.0 MHz, CDCl3) d 1.4 (d, 6H), 4.48-4.52 (m, 1H), 7.0 (br s, 2H), 7.5-7.7 (m, 5H), 7.7-7.75 (m, 1H), 8.2 (d, 1H), 8.3 (d, 1H) and 8.55 (s, 1H) ppm; MS (ES+) 422.2

Workup

  1. customThe layers were separated
  2. washthe organic layer was washed with dilute NaHCO3 solution (1×10 mL) and brine (1×10 mL)
  3. concentrationconcentrated in vacuo
  4. customto leave a solid
  5. customThe solid was purified by column chromatography on silica eluting with 50% ether/petroleum ether

Sources & evidence

ORD record
ord-95ecd09e33bc432c8f1443a52fa9cabe
Source dataset
uspto-grants-2014_09
Patent number
US08841308B2

Reaction notes

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