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

HRID 2380609Notes

Reaction equation

HRID 2380609 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 headed 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%).

Workup

  1. waitto stand at room temperature for 16 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-056fa08881464996887f26a30ec8badd
Source dataset
uspto-grants-1994_11
Patent number
US05369107

Reaction notes

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