Hydrochloric Acid → HCID 178508563, compound

HRID 1657004Notes

Reaction equation

HRID 1657004 reaction equation
C([NH:4][C:5]1[S:6][C:7]([S:10][C:11]2[N:16]=[C:15]([OH:17])[CH:14]=[CH:13][N:12]=2)=[CH:8][N:9]=1)(=O)C.O1CCCC1.Cl>C(O)C>[NH2:4][C:5]1[S:6][C:7]([S:10][C:11]2[N:16]=[C:15]([OH:17])[CH:14]=[CH:13][N:12]=2)=[CH:8][N:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 178474459HCID 178474459, compound

Product 1

HCID 178508563HCID 178508563, compoundYield 14.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-acetylamino-5-(4-hydroxypyrimidin-2-ylthio)thiazole (3.7 g) in a mixture of ethanol (100 ml), tetrahydrofuran (40 ml) and aqueous 6N-hydrochloric acid (20 ml) was refluxed for 6.5 hours with stirring. The reaction mixture was concentrated under reduced pressure and the residue was dissolved in water. The solution was adjusted to pH 8.5 using aqueous sodium bicarbonate. The precipitates were collected by filtration, washed with water and dried in vacuo to give solid. The solid was subjected to column chromatography on silica gel (silica gel 60, 70-230 mesh; Merck: 250 g) and eluted with a mixture of chloroform and methanol (10:1). The fractions containing the objective compound were combined and concentrated under reduced pressure to give 2-amino-5-(4-hydroxypyrimidin-2-ylthio)thiazole (0.45 g, yield: 14.5%). mp: 210°-220° C. (dec.) IR (Nujol): 3450, 3350, 3125, 1675, 1510,1230 cm-1

Workup

  1. temperaturewas refluxed for 6.5 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in water
  4. filtrationThe precipitates were collected by filtration
  5. washwashed with water
  6. customdried in vacuo
  7. customto give solid
  8. washeluted with a mixture of chloroform and methanol (10:1)
  9. additionThe fractions containing the objective compound
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-27fe4310595c4ccc81d012c916967cc1
Source dataset
uspto-grants-1993_10
Patent number
US05256675

Reaction notes

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