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Structure of 6125-37-7

Chemical Structure| 6125-37-7

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Product Details of [ 6125-37-7 ]

CAS No. :6125-37-7
Formula : C9H11ClN2O3S
M.W : 262.71
SMILES Code : O=C(C1=C(C)N=C(NC(CCl)=O)S1)OCC
MDL No. :MFCD02251156

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Application In Synthesis of [ 6125-37-7 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 6125-37-7 ]

[ 6125-37-7 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 7210-76-6 ]
  • [ 79-04-9 ]
  • [ 6125-37-7 ]
YieldReaction ConditionsOperation in experiment
90% 50 mmol of 2-amino-4-methylthiazole-5-carboxylic acid ethyl ester, 100 mmol of anhydrous potassium carbonate, 100 mL of dichloromethane, stirred at room temperature for 30 min, dropping 8. OmL of chloroacetyl chloride at room temperature The The reaction solution was poured into ice water, extracted with dichloromethane, washed with saturated brine, washed with saturated sodium carbonate solution, washed with water, dried over anhydrous sodium sulfate, and the crystals were recrystallized from ethanol / water to obtain white crystals 2-(2-chloroacetylamino)-4-methylthiazole-5-carboxylic acid ethyl ester in 90%
85% With triethylamine; In tetrahydrofuran; at 0 - 5℃; for 3h; Triethylamine (2.45 g, 24.19 mmol) was added to a solution of ethyl 2-amino-4-methylthiazole-5-carboxylate (1) (3g, 16.12 mmol) in THF (80 mL) in an ice bath. 2-chloroacetyl chloride (1.52 g, 19.35 mmol) mixed with THF (10 mL) and added dropwise to the mixture. The mixture was stirred for 3 h in an ice bath. The reaction was monitored with TLC (EtOAc:PET 1:1). After the reaction was completed, THF was removed, and the crude product was washed with water. Yield 85% [29].
84% In toluene; for 6h;Reflux; Chloroacetyl chloride (0.85 g, 7.5 mmol) was added dropwise to a stirred solution of the thiazole 1 (0.93 g, 5 mmol) in dry toluene (15 mL) at room temperature. The reaction mixture was heated under reflux for 6 h, then the solvent was removed under reduced pressure and the remaining pale yellow residue was treated with water, filtered, dried and recrystallized. Physicochemical and analytical data are recorded in Table 3. IR (cm-1): 3215 (NH), 1690 (C=O), 1645 (C=O). 1H NMR (δ-ppm): 1.34 (t, J = 9 Hz, 3H, ester- CH3), 2.61 (s, 3H, Thiazol-C4-CH3), 4.29 (q, J=9 Hz, 2H, ester- CH2), 4.41 (s, 2H, CH2-Cl), 8.12 (brs, 1H, NH). 13C NMR (δ-ppm): 6.8 (CH3), 13.4 (CH3), 48.8 (CH2Cl), 59.0 (CH2), 104.0, 149.3, 172.1 (Thiazole C), 163.2 (CO), 168.1 (CO).
59% With potassium carbonate; In toluene;Reflux; General procedure: A solution of ethyl 2-amino-4-methylthiazole-5-carboxylate (24, 1.8 g, 0.01 mol), potassium carbonate (2.07 g, 0.015 mol) in dry toluene (50 ml) was stirred at room temperature, while 2-chloroacetyl chloride (3, 1.7 g, 1.2 ml, 0.015 mol) or 3-chloropropionyl chloride (4, 1.9 g, 1.4 ml. 0.015 mol), was added dropwise. The reaction mixture was heated under reflux for 4-6 h, and continued as mentioned under compounds 5-8, (Table 1).
With triethylamine; In tetrahydrofuran; at 0 - 20℃; General procedure: A solution of 2-amino-5-substituted-4-methylthiazole (1) (0.01 mol) (1a:1.2 g, 1b:1.3 g, 1c:1.6 g, 1d:1.9 g, 1e:1.9 g)[29, 30] and triethylamine (0.01 mol) (1.5 mL) was prepared by stirring in THF (50 mL) at room temperature. After cooling the mixture in an ice bath, chloroacetyl chloride (0.01mol) (0.8 mL) was added drop wise with constant stirring. Before evaporation of the solvent under reduced pressure,the reaction mixture was further stirred for 1 hour at room temperature. The precipitate formed was crystallised from ethanol [31, 12].
With triethylamine; In tetrahydrofuran; at 0 - 5℃; General procedure: 2-Chloro-N-(thiazol-2-yl/benzothiazol-2-yl)acetamidederivatives Thiazole/benzothiazole derivative (10 mmol) was solved in THF(200 mL). After triethylamine (12 mmol, 1.67 mL) was addedto the solution, chloroacetyl chloride (12 mmol, 0.96 mL) wasadded dropwise at 0-5Candthemixturewasstirredfor3-5h.After the reaction completed, the mixture was poured into icewater and the collapsed raw product was filtered and dried.
With potassium carbonate; In dichloromethane; General procedure: Aminothiazole (A1-A18, 50 mmol) and 100 mmol of potassiumcarbonate were dissolved in dichloromethane (100 mL), chloroacetylchloride (8.0 mL) was added dropwise under ice bath, andreacted at room temperature monitored by TLC. When the reactionis completed, the reaction solution is poured into water, andwashed with sodium bicarbonate solution, saturated saline andwater successively, dry the organic phase with anhydrous sodiumsulfate, remove the solvent under reduced pressure, and recrystallizewith ethanol to obtain raw product B1-B18. Then intermediate(30 mmol) and KSCN (45 mmol) were dissolved in 100 mLof ethanol, and reflux for 6 h. The reaction mixture were cooleddown, filtered, and washed with ethanol and water, the crudeproduct was recrystallized from ethanol/water to afford the pure 4-thiazolinone intermediate C1-C18.2-(4-Thiazolinone-2-imino)-4-methylthiazole-5-carboxylicacid ethyl ester (C1). Yellow solid. m.p. 203-204 C, yield 81.9%. 1HNMR (400 MHz, DMSO-d6) δ: 1.27 (t, J 7.2 Hz, 3H, CH3), 2.58 (s, 3H,CH3), 4.03 (s, 2H, SCH 2), 4.25 (q, J 7.2 Hz, 2H, OCH2), 12.28 (s, 1H,NH); 13C NMR (150 MHz, DMSO-d6) δ: 14.62, 17.84, 35.68, 61.29,117.06, 158.03, 162.06, 166.69, 171.08, 174.58; Anal. Calcd. forC10H11N3O3S2: C, 42.09; H, 3.89; N, 14.73; found C, 42.05; H, 3.40; N,14.71.

 

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