Chlorosuccinimide → 5-Chloro-4-(pyridin-3-yl)-thiazol-2-amine

HRID 653610Notes

Reaction equation

HRID 653610 reaction equation
[Cl:1]N1C(=O)CCC1=O.[N:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]2[N:16]=[C:17]([NH2:20])[S:18][CH:19]=2)[CH:10]=1>CN(C)C=O>[Cl:1][C:19]1[S:18][C:17]([NH2:20])=[N:16][C:15]=1[C:11]1[CH:10]=[N:9][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 1548934-(3-Pyridinyl)-2-thiazolamine

Product 1

HCID 129408895-Chloro-4-(pyridin-3-yl)-thiazol-2-amineYield 86.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-Chlorosuccinimide (14,7 g) was added all at once to a solution of 4-(pyridin-3-yl)-thiazol-2-amine (17,7 g) in N,N-dimethylformamide (130 ml) at 0°-5° C. After five minutes, the product precipitated, and after ten minutes, precipitation was completed by addition of water and ammonium hydroxide solution. The product was filtered and dried in vacuo at 60° C. to give 5-chloro-4-(pyridin-3-yl)-thiazol-2-amine, (18,2 g) Mp 202° C.

Workup

  1. customthe product precipitated
  2. waitafter ten minutes
  3. customprecipitation
  4. additionwas completed by addition of water and ammonium hydroxide solution
  5. filtrationThe product was filtered
  6. customdried in vacuo at 60° C.

Sources & evidence

ORD record
ord-920bed1915804310a576375bfcba9a2d
Source dataset
uspto-grants-1992_07
Patent number
US05128340

Reaction notes

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