HCID 19100759, compound → HCID 19100785, compound

HRID 1974995Notes

Reaction equation

HRID 1974995 reaction equation
O.[CH3:2][C:3]1[C:11]2[NH:10][C:9](=[O:12])[C:8](=[O:13])[NH:7][C:6]=2[S:5][CH:4]=1.[I:14](Cl)(=O)=O.I(Cl)(=O)=O.C([N+](C)(C)C)C1C=CC=CC=1>C(O)(=O)C.[Cl-].[Zn+2].[Cl-]>[I:14][C:4]1[S:5][C:6]2[NH:7][C:8](=[O:13])[C:9](=[O:12])[NH:10][C:11]=2[C:3]=1[CH3:2]

Participants

5

Reactant 2

HCID 19100759HCID 19100759, compoundHCID 56924451Trimethylbenzylammonium Dichloroiodate

Product 1

HCID 19100785HCID 19100785, compoundYield 24.7%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 176Acetic AcidSolvent

Procedure

7-Methylthieno[2,3-b)pyrazine-2,3(1H,4H)-dione hydrate (1.0 g, 5.0 mmol) was suspended in 60 ml of acetic acid and benzyltrimethylammonium dichloroiodate 95% (2.1 g, 5.75 mmol) and zinc chloride (1.64 g, 12.0 mmol) was added. The mixture was stirred for 4.5 h at room temperature, the precipitate was filtered off, washed with acetic acid, water and dried. The crude compound (1.13 g) was recrystallized from acetic acid/water and twice from ethanol to give 0.38 g (24%) of the title compound. Decomp. above 240° C. 1H-NMR (DMSO-D6, δ): 2.12 (s, 3H), 11.98 (s, 1H), 12.22 (s, 1H).

Workup

  1. filtrationthe precipitate was filtered off
  2. washwashed with acetic acid, water
  3. customdried
  4. customThe crude compound (1.13 g) was recrystallized from acetic acid/water and twice from ethanol

Sources & evidence

ORD record
ord-6a8c427a58d54ae89884e9a10e9baf23
Source dataset
uspto-grants-1994_02
Patent number
US05284847

Reaction notes

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