[ CAS No. 104146-17-0 ]

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CAS No. 104146-17-0, is a thiazoles compound, with a molecular weight of 147.58, molecular formula C4H2ClNOS, Ambeed provides reports for batches of (such as NMR, HPLC/GC).

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Product Details

CAS No. :104146-17-0MDL No. :MFCD09837291
Formula :C4H2ClNOSInChI Key :GJTWEAFBOIYNLZ-UHFFFAOYSA-N
M.W :147.58Pubchem ID :14501317
Boiling Point :254.6буC at 760 mmHg
Synonyms :

Computed Properties

TPSA : 58.2 H-Bond Acceptor Count : 3
XLogP3 : 1.7 H-Bond Donor Count : 0
SP3 : 0.00 Rotatable Bond Count : 1

Safety

Signal Word:WarningClassN/A
Precautionary Statements:P261-P280-P305+P351+P338UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis

[ 104146-17-0 ] Synthesis Path-Upstream   1~4

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YieldReaction ConditionsOperation in experiment
95% With hydrogenchloride In tetrahydrofuran; 1,4-dioxane; water at 20℃; for 3.00 h; [000273] Synthesis of 4-chlorothiazole-5-carbaldehyde (333): To a stirred solution of compound 332 (1.1 g, 5.75 mmol) in THF (10 mL) was added 5 N aqueous HC1 in 1, 4-dioxane (6 mL) at 0 °C; warmed to RT and stirred for 3 h. The reaction was monitored by TLC; after completion of the reaction, the reaction mixture was poured into brine (20 mL) extracted with EtOAc (2 x 50 mL). The combined organic extracts were washed with saturated sodium bicarbonate (100 mL) dried over sodium sulfate, filtered and concentrated in vacuo to afford compound 333 (800 mg, 95percent) as yellow oil. TLC: 10percent EtOAc/ hexanes (R 0.3); 1H NMR (CDC13, 500 MHz): ö 10.11 (s, 1H), 9.00 (s, 1H).
92%
Stage #1: With hydrogenchloride; water In tetrahydrofuran at 20℃; for 2.00 h;
Stage #2: With sodium hydrogencarbonate In tetrahydrofuran; water
Step 4. 4-chloro-1,3-thiazole-5-carbaldehydeTo a solution of 4-chloro-5-(1,3-dioxolan-2-yl)-1,3-thiazole (0.75 g, 3.9 mmol) in THF (10 mL) was added 5.0 M of HCl solution in water (2 mL, 10 mmol). The resulting mixture was stirred at ambient temperature for 2 h. The reaction solution was poured into brine and extracted with ethyl acetate three times. The combined extracts were washed with saturated sodium bicarbonate, brine, dried over MgSO4, filtered, and concentrated to give the desired product as an off-white solid (0.53 g, 92percent). 1H NMR (300 MHz, CDCl3): δ 10.16 (s, 1H), 9.03 (s, 1H).
88% With hydrogenchloride In tetrahydrofuran at 20℃; for 1.50 h; Add 5 N HC1 (50 mL, 250 mmol) to a stirred solution of 4-chloro-5- [1, 3] dioxolan-2- yl-thiazole (19.2482 g, 100 mmol) and tetrahydrofuran (250 mL). Stir the reaction for 1.5 h at room temperature. Pour the reaction into brine (300 mL) and extract with ethyl acetate (3 X 100 mL). Wash the ethyl acetate with saturated sodium bicarbonate (150 mL) and then with brine (100 mL). Dry the ethyl acetate over sodium sulfate and filter off the sodium sulfate. Concentrate on a rotary evaporator and purify the crude product by flash chromatography on silica gel eluting with 20 percent ethyl acetate/hexanes to yield 13. 09 g (88percent) of4-chloro-thiazole-5-carbaldehyde : IHNMR (CDCl3) : 5 = 10. 13 (s, 1H), 9.04 (s, 1H).
38% With hydrogenchloride; n-butyllithium In tetrahydrofuran; hexane c)
4-Chloro-thiazole-5-carbaldehyde

A 1.6 M solution of n-butyl-lithium in hexane (2.7 mL, 4.32 mmol) was added dropwise to a stirred solution of 4-chloro-5-[1,3]dioxolan-2-yl-thiazole (787.2 mg, 4.32 mmol) and tetrahydrofuran (20.0 mL) in an ice bath.
The solution was stirred for 1 h, equilibrated to room temperature, and poured into a 10percent aqueous hydrochloric acid solution (50 mL).
The solution was extracted with ether (100 mL).
To the extracts were added 10percent aqueous hydrochloric acid solution and the resultant solution was stirred for 6 h.
The ether layer was washed with brine, dried over sodium sulfate, decanted, and concentrated.
The product was purified by column chromatography (dichloromethane) to yield 245 mg (38percent) of the title compound as an off-white solid. 1H NMR (CDCl3): 10.11 (s, 1H), 9.01 (s, 1H).

Reference: [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
[6] Patent: WO2015/193506, 2015, A1. Location in patent: Page/Page column 51
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Reference: [1] Patent: US4839350, 1989, A
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Reference: [1] Patent: US4839350, 1989, A
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Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1992, # 8, p. 973 - 978
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