Acetic Acid → HCID 15729178, compound

HRID 1656977Notes

Reaction equation

HRID 1656977 reaction equation
[NH2:1][C:2]1[S:3][C:4]([S:7][C:8]2[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=2)=[CH:5][N:6]=1.[C:15](O)(=[O:17])[CH3:16]>C(OC(=O)C)(=O)C>[NH2:1][C:2]1[S:3][C:4]([S:7][C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:15](=[O:17])[CH3:16])=[CH:10][CH:9]=2)=[CH:5][N:6]=1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 18954726HCID 18954726, compound

Product 1

HCID 15729178HCID 15729178, compoundYield 44.2%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

A mixture of 2-amino-5-(4-aminophenylthio)thiazole, (4.0 g) in a mixture of acetic acid (40 ml) and acetic anhydride (2.2 g) was stirred at room temperature for 4 hours. The reaction mixture was concentrated under reduced pressure and the residue was triturated with 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: 150 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-acetylaminophenylthio)thiazole (2.1 g, yield: 44.2%). mp: 240°-245° C. (dec.)

Workup

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

Sources & evidence

ORD record
ord-15a0c43ae31849daad676701a4f63535
Source dataset
uspto-grants-1993_10
Patent number
US05256675

Reaction notes

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