| Identification | Back Directory | [Name]
4-Chlorothiazole-5-carboxaldehyde | [CAS]
104146-17-0 | [Synonyms]
4-Chlorothiazole-5-carbaldehyde
4-chloro-5-thiazolecarboxaldehyde
4-Chlorothiazole-5-carboxaldehyde
5-Thiazolecarboxaldehyde, 4-chloro-
4-chloro-1,3-thiazole-5-carbaldehyde
5-Thiazolecarboxaldehyde, 4-chloro- (9CI) | [Molecular Formula]
C4H2ClNOS | [MDL Number]
MFCD09837291 | [MOL File]
104146-17-0.mol | [Molecular Weight]
147.58 |
| Chemical Properties | Back Directory | [storage temp. ]
Inert atmosphere,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 |
| Hazard Information | Back Directory | [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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