Hydrochloric Acid → 2-Amino-5-chloro-4-(4-pyridylthiomethyl)thiazole

HRID 1656969Notes

Reaction equation

HRID 1656969 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][N:15]=[CH:14][CH:13]=1.O1CCCC1.Cl>C(O)C>[NH2:7][C:5]1[S:6][C:2]([Cl:1])=[C:3]([CH2:10][S:11][C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)[N:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 157291695-Chloro-2-formylamino-4-(4-pyridylthiomethyl)thiazole

Product 1

HCID 189547322-Amino-5-chloro-4-(4-pyridylthiomethyl)thiazoleYield 56.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 5-chloro-2-formylamino-4-(4-pyridylthiomethyl)thiazole (4.9 g) in a mixture of ethanol (25 ml), tetrahydrofuran (20 ml) and concentrated hydrochloric acid (7 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 under ice-cooling. The precipitates were collected by filtration, washed with water and dried in vacuo to give 2-amino-5-chloro-4-(4-pyridylthiomethyl)thiazole (0.26 g, yield: 56.6%). IR (Nujol): 3350, 3250, 1685, 1530 cm-1

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in water
  3. temperaturecooling
  4. filtrationThe precipitates were collected by filtration
  5. washwashed with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-d3dc3efbfdc34ac99a0f3d9f276a44d1
Source dataset
uspto-grants-1993_10
Patent number
US05256675

Reaction notes

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