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Acetic Acid → [1,3]Thiazolo[4,5-b]pyrazine-2(3H)-thione

HRID 1947450
Notes
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Reaction equation

HRID 1947450 reaction equation
[NH2:1][C:2]1[C:7](Cl)=[N:6][CH:5]=[CH:4][N:3]=1.O(CC)[C:10]([S-:12])=[S:11].[K+].CN1CCCC1=O.C(O)(=O)C>O>[S:12]1[C:7]2[C:2](=[N:3][CH:4]=[CH:5][N:6]=2)[NH:1][C:10]1=[S:11]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 13387N-methyl-2-pyrrolidoneHCID 2762242-Amino-3-chloropyrazineHCID 2735045Potassium ethylxanthate

Product 1

HCID 13772324[1,3]Thiazolo[4,5-b]pyrazine-2(3H)-thioneYield 67%

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Conditions

Temperature
150 °C

Procedure

To a mixture of 2-amino-3-chloropyrazine (5 g, 38.6 mmol) and potassium ethyl xanthate (9.28 g, 57.9 mmol) was added 1-methyl-2-pyrrolidinone (68 mL) and the solution was heated (150° C., 16 h). The suspension was cooled (rt) and treated with glacial acetic acid (10 mL) and H2O (1500 mL). The suspension was filtered and the resulting solid was suspended and sonicated in ethanol:H2O (1:1, 500 mL). The suspension was filtered and the solid was washed with H2O, dried (calcium sulfate) in vacuo to yield the title compound as a solid (4.36 g, 67%). MS (ESI): mass calculated for C5H3N3S2, 168.98; m/z found, 170.00 [M+H]+. 1H NMR (500 MHz, DMSO-d6): 14.69 (s, 1H), 8.42 (d, J=2.8, 1H), 8.39 (d, J=2.8, 1H).

Workup

  1. temperatureThe suspension was cooled (rt)
  2. filtrationThe suspension was filtered
  3. customsonicated in ethanol:H2O (1:1, 500 mL)
  4. filtrationThe suspension was filtered
  5. washthe solid was washed with H2O
  6. dry with materialdried (calcium sulfate) in vacuo

Sources & evidence

ORD record
ord-7559fb1e5af0497faeaf29f400b18f81
Source dataset
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08399465B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes