Chlorosuccinimide → 5-Chloro-2-formylamino-4-(4-pyridylthiomethyl)thiazole

HRID 1656968Notes

Reaction equation

HRID 1656968 reaction equation
[CH:1]([NH:3][C:4]1[S:5][CH:6]=[C:7]([CH2:9][S:10][C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)[N:8]=1)=[O:2].[Cl:17]N1C(=O)CCC1=O>C(O)(=O)C>[Cl:17][C:6]1[S:5][C:4]([NH:3][CH:1]=[O:2])=[N:8][C:7]=1[CH2:9][S:10][C:11]1[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 15729168HCID 15729168, compound

Product 1

HCID 157291695-Chloro-2-formylamino-4-(4-pyridylthiomethyl)thiazoleYield 46.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 2-formylamino-4-(4-pyridylthiomethyl)thiazole (1.6 g) and N-chlorosuccinimide (1.5 g) in acetic acid (25 ml) was heated at 40°-50° C. for 5 hours with stirring and then the mixture was allowed to stand at room temperature for 16 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 5-chloro-2-formylamino-4-(4-pyridylthiomethyl)thiazole (0.85 g, yield: 46.8%). mp: 200°-203° C. (dec.) IR (Nujol): 1680, 1665, 1587, 1300 cm-1

Workup

  1. temperaturewas heated at 40°-50° C. for 5 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe residue was triturated with aqueous sodium bicarbonate
  4. filtrationThe precipitates were collected by filtration
  5. washwashed with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-f074c0db8c9941cc8392e977537fb9a9
Source dataset
uspto-grants-1993_10
Patent number
US05256675

Reaction notes

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