Ammonia → 2-Chloro-1,3-thiazole-5-carboxamide

HRID 747555Notes

Reaction equation

HRID 747555 reaction equation
[Cl:1][C:2]1[S:3][C:4]([C:7]([O:9]CC)=O)=[CH:5][N:6]=1.[NH3:12]>CO>[Cl:1][C:2]1[S:3][C:4]([C:7]([NH2:12])=[O:9])=[CH:5][N:6]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 19017727Ethyl 2-chloro-1,3-thiazole-5-carboxylate

Product 1

HCID 534244962-Chloro-1,3-thiazole-5-carboxamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

Dissolve ethyl 2-chlorothiazole-5-carboxylate (0.927 g, 4.84 mmol) in methanol. Cool the solution to 0° C., then bubble NH3 into the reaction mixture for 10 minutes. Then seal the reaction vessel and stir for 3 hours. Concentrate the reaction mixture to give the title product: 1H NMR (CDCl3): 8.21 (s, 1H), 8.19 (s, 1H), 7.77 (s, 1H); HPLC [YMC-Pro pack C-18 (150×4.6 mm, S-5 microm), 0.05% TFA/acetonitrile in 0.05% TFA/water at 1.0 mL/min, 10-20% over 5 min, 20-95% over 18], tR=6.9 min, 100% purity.

Workup

  1. customThen seal the reaction vessel
  2. concentrationConcentrate the reaction mixture

Sources & evidence

ORD record
ord-0a6cf79ad19544158e674e2534061340
Source dataset
uspto-grants-2008_07
Patent number
US07396943B2

Reaction notes

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