Hydrochloric Acid → 2-Amino-4-(4-aminophenylthiomethyl)-5-chlorothiazole

HRID 1656974Notes

Reaction equation

HRID 1656974 reaction equation
[Cl:1][C:2]1[S:6][C:5]([NH:7]C=O)=[N:4][C:3]=1[CH2:10][S:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18]C=O)=[CH:14][CH:13]=1.Cl.CO>O1CCCC1>[NH2:7][C:5]1[S:6][C:2]([Cl:1])=[C:3]([CH2:10][S:11][C:12]2[CH:13]=[CH:14][C:15]([NH2:18])=[CH:16][CH:17]=2)[N:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 157291735-Chloro-2-formylamino-4-(4-formylaminophenylthiomethyl)thiazole

Product 1

HCID 157291742-Amino-4-(4-aminophenylthiomethyl)-5-chlorothiazoleYield 79.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5-chloro-2-formylamino-4-(4-formylaminophenylthiomethyl)thiazole (3.5 g) in a mixture of concentrated hydrochloric acid (9 ml), methanol (30 ml) and tetrahydrofuran (30 ml) was stirred at room temperature for 4 hours. The reaction mixture was concentrated under reduced pressure and the residue was dissolved in water. The solution was adjusted to pH 8 using aqueous sodium bicarbonate with stirring under ice cooling. 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-4-(4-aminophenylthiomethyl)-5-chlorothiazole (2.3 g, yield: 79.3%). mp: 158°-163° C. (dec.)

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in water
  3. stirringwith stirring under ice cooling
  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-aa39f29088174ab4a6969784ff25c440
Source dataset
uspto-grants-1993_10
Patent number
US05256675

Reaction notes

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