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

HRID 547338Notes

Reaction equation

HRID 547338 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]

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 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

To a mixture of 2-amino-3-chloropyrazine (5.0 g, 38.6 mmol) and potassium ethyl xanthate (9.28 g, 57.9 mmol) was added 1-methyl-2-pyrrolidinone (68 mL). The solution was stirred and heated at 150° C. for 16 h. After cooling to rt, glacial acetic acid (10 mL) and water (1500 mL) were added to the solution. The solid precipitate was filtered. The solid was suspended in 1:1 EtOH/water (500 mL) and sonicated. The solid was once again filtered, washed with water, and dried with CaSO4 in vacuo for 16 h to yield the product (4.36 g, 67%). 1H NMR (500 MHz, DMSO-d6): 14.69 (br s, 1H), 8.42 (d, J=2.8, 1H), 8.39 (d, J=2.8, 1H). MS (ESI): mass calcd. for C5H3N3S2, 168.98; m/z found, 170.00 [M+H]+.

Workup

  1. temperatureAfter cooling to rt
  2. filtrationThe solid precipitate was filtered
  3. customsonicated
  4. filtrationThe solid was once again filtered
  5. washwashed with water
  6. dry with materialdried with CaSO4 in vacuo for 16 h

Sources & evidence

ORD record
ord-3f0baaf0146a4650baa2d9e914070415
Source dataset
uspto-grants-2011_05
Patent number
US07939527B2

Reaction notes

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