Chlorosuccinimide → Aminothiazole 20

HRID 1355431Notes

Reaction equation

HRID 1355431 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8]1[S:9][CH:10]=[CH:11][N:12]=1.[Cl:13]N1C(=O)CCC1=O>>[Cl:13][C:10]1[S:9][C:8]([NH:7][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)=[N:12][CH:11]=1

Participants

3

Reactant 2

HCID 31398ChlorosuccinimideHCID 956683N-(pyridin-2-yl)thiazol-2-amine

Product 1

HCID 5329401Aminothiazole 20

Procedure

Pyridin-2-yl-thiazol-2-yl-amine (5-2) and 1.2 equivalents of N-chlorosuccinimide were combined in a flame dried flask and allowed to stir together overnight under argon in anhydrous dioxane (0.25 M). The dioxane solution was then diluted with water and the resulting product filtered off. 1H-NMR (DMSO-d6) δ11.463 (1H,s) 8.30 (dd, 1H, J=4.9, 0.9 Hz) 7.73 (t, 1H, J=8.42 Hz) 7.38 (s, 1H) 7.03 (d, 1H, J=8.4 Hz) 6.96 (t, 1H, J=5.9 Hz). MS [M+H]+=211.9.

Workup

  1. customdried flask
  2. additionThe dioxane solution was then diluted with water
  3. filtrationthe resulting product filtered off

Sources & evidence

ORD record
ord-f640a364b90c441590bef2f10d818d31
Source dataset
uspto-grants-2003_07
Patent number
US06586423B2

Reaction notes

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