4-Chlorothiazole-5-carboxaldehyde Chemical Properties

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

Appearance

Light yellow to yellow Solid

InChI

InChI=1S/C4H2ClNOS/c5-4-3(1-7)8-2-6-4/h1-2H

InChIKey

GJTWEAFBOIYNLZ-UHFFFAOYSA-N

SMILES

S1C(C=O)=C(Cl)N=C1

Safety Information

HS Code 

2934999090

4-Chlorothiazole-5-carboxaldehyde Usage And Synthesis

Synthesis

General procedure for the synthesis of 4-chlorothiazole-5-carbaldehyde (333): to a stirred solution of 4-chloro-5-(1,3-dioxolan-2-yl)thiazole (332, 1.1 g, 5.75 mmol) in THF (10 mL) was slowly added an aqueous 5N HCl solution (6 mL) at 0°C. The reaction mixture was gradually warmed up to room temperature and stirred continuously for 3 hours. The reaction progress was monitored by TLC. After completion of the reaction, the mixture was poured into brine (20 mL) and extracted with EtOAc (2 x 50 mL). The organic phases were combined, washed with saturated sodium bicarbonate solution (100 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford the target product 4-chlorothiazole-5-carbaldehyde (333, 800 mg, 95%) as a yellow oil.TLC conditions: 10% EtOAc/hexanes (Rf=0.3); 1H NMR (CDCl3, 500 MHz): δ 10.11 (s, 1H), 9.00 (s, 1H).

References

[1] Patent: WO2015/138895, 2015, A1. Location in patent: Paragraph 000273
[2] Patent: US2010/298334, 2010, A1. Location in patent: Page/Page column 78
[3] Patent: WO2005/92885, 2005, A1. Location in patent: Page/Page column 94
[4] Patent: US2003/45546, 2003, A1
[5] Patent: WO2010/132999, 2010, A1. Location in patent: Page/Page column 148

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