Acetic Acid → HCID 178419408, compound

HRID 2401731Notes

Reaction equation

HRID 2401731 reaction equation
[Br:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]1[NH:11][CH:10]=[N:9][N:8]=1.II.[I:14](O)(=O)(=O)=O.C(O)(=O)C.O.S(=O)(=O)(O)O>>[Br:1][C:2]1[CH:6]=[C:5]([I:14])[S:4][C:3]=1[C:7]1[NH:11][CH:10]=[N:9][N:8]=1

Participants

7

Reactant 6

HCID 176Acetic AcidHCID 807IodineHCID 962WaterHCID 1118Sulfuric AcidHCID 65185Metaperiodic acidHCID 178419415HCID 178419415, compound

Product 1

HCID 178419408HCID 178419408, compoundYield 100%

Procedure

To a mixture of 3-(3-bromo-2-thienyl)-4H-1,2,4-triazole (1.12 g, 4.87 mmol), iodine (1.12 g, 4.41 mmol) and periodic acid (4.80 g, 24.8 mmol) in acetic acid (11.0 mL, 200 mmol) were added water (8.0 mL, 400 mmol) and sulfuric acid (2.0 mL, 40 mmol) and the reaction mixture was stirred at rt for two days. The resulting white precipitate was collected by filtration. The solid cake was washed with water and dried under high vacuum at 40° C. to yield product as a white solid (1.74 g, 100% yield, as a white solid). LCMS: (FA) ES+, 357.7. 1H NMR (400 MHz, d6-DMSO) δ: 8.63 (s, 1H), 7.43 (s, 1H)

Workup

  1. filtrationThe resulting white precipitate was collected by filtration
  2. washThe solid cake was washed with water
  3. customdried under high vacuum at 40° C.
  4. customto yield product as a white solid (1.74 g, 100% yield

Sources & evidence

ORD record
ord-2a124085c2a941a4bb5224e01179c41a
Source dataset
uspto-grants-2014_08
Patent number
US08796268B2

Reaction notes

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