Structure of 88-11-9
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| CAS No. : | 88-11-9 |
| Formula : | C5H10ClNS |
| M.W : | 151.66 |
| SMILES Code : | ClC(N(CC)CC)=S |
| English Name : | Diethylthiocarbamoyl chloride |
| MDL No. : | MFCD00022106 |
* 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.

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With water |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With tetrachloromethane; water |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| In benzene Heating; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 66% | With pyridine; hexamethyldisilathiane Heating; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 84% | With potassium hydroxide In tetrahydrofuran; water at 20℃; for 16h; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 95% | Stage #1: 5-hydroxyquinoxaline With potassium carbonate In N,N-dimethyl-formamide at 23℃; for 1h; Stage #2: N,N-diethylthiocarbamoyl chloride In N,N-dimethyl-formamide for 2h; | 8.A A. Diethylthiocarbamic acid O-quinoxalin-5-yl ester. ; A mixture of 5-hydroxyquinoxaline (2.13 g, 14.6 mmol), finely ground K2CO3 (4.0 g, 29 mmol), and DMF (50 mL) was stirred at 23° C. for 1 h. Solid diethylthiocarbamoyl chloride (2.439 g, 16.1 mmol) was then added. The resulting mixture was stirred for 2 h, then was diluted with water (150 mL) and extracted with Et2O (2×100 mL). The combined organic extracts were washed with water (100 mL) and brine (100 mL), then dried and concentrated to a viscous orange oil, which was used without purification (3.63 g, 95%). MS (ESI+): mass calcd. for C13H15N3OS, 261.1; m/z found, 262 [M+H]+. 1H NMR (500 MHz, CDCl3): 8.85-8.65 (m, 2H), 7.96 (dd, J=8.5, 1.1, 1H), 7.71 (t, J=7.9, 1H), 7.46 (dd, J=7.6, 1.2, 1H), 3.87 (q, J=7.1, 2H), 3.78 (q, J=7.1, 2H), 1.38 (t, J=7.1, 3H), 1.28 (t, J=7.1, 3H). 13C NMR (125 MHz, CDCl3): 186.6, 149.4, 144.9, 144.5, 143.4, 137.0, 128.9, 127.0, 123.1, 48.2, 44.5, 13.1, 11.5. |
| With potassium carbonate In N,N-dimethyl-formamide at 23℃; for 2h; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With sodium | 33 EXAMPLE 33 EXAMPLE 33 This example describes the preparation of 3'-(diethylthiocarbamoyloxy)propionanilide. A reaction vessel containing 33 parts of the sodium with phenate of 3'-hydroxypropionanilide is charged with 32 parts of diethylthiocarbamoyl chloride, the temperature increasing to a maximum of about 85°C. The reaction mixture is heated at 100°C for 15 minutes, cooled to 60°C and filtered. The filtrate is allowed to stand for 16 hours and a resinous material separates. The resinous material is crystallized from methyl alcohol and air dried to give 22 parts of product, m.p. 140°-141°C. Calc'd for C14 H20 N2 O2 S: C, 59.97; H, 7.90; S, 11.44. Found: C, 59.85; H, 7.43; S, 11.47. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 88.2% | With triethylamine In 1,2-dichloro-ethane at 25 - 35℃; for 2h; Large scale; | 5.b; 6.b b. In the reaction flask, add 840.8 g of 4-hydroxypyrazole, 1062.5 g of triethylamine, 3363.2 g of dichloroethane, and stir.Dissolve,The above intermediate II solution was slowly added dropwise to the system, the reaction temperature was maintained at 25-35 ° C, and the incubation reaction was carried out for 2 hours.Adjust the pH to 6-7 with concentrated hydrochloric acid, and dispense.The organic phase is desolved to obtain the crude intermediate II, and the crude product is recrystallized from ethanol.Drying under reduced pressure gave intermediate III 1757.2 g.The yield was 88.2%, and the liquid phase content was 99.3%. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 91% | With sodium hydride In tetrahydrofuran; mineral oil at 25℃; for 1h; Inert atmosphere; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 62% | In acetonitrile at 20℃; for 12h; | 4.2.5 Bis(diethylamino thiocarbonyl)-monosulfide (1e) To the triethylammonium diethylcarbamodithioate (2.2mmol) in acetonitrile (20mL) was added diethylcarbamothioic chloride (272mg, 2.2mmol) and the mixture was stirred at room temperature overnight. The solvent was evaporated under reduced pressure and residue was diluted with ethyl acetate and washed with water, brine, and dried over Na2SO4, filtered, concentrated in vacuo. Then the residue was purified on a silica gel column to give 1e. Yellow oil. 62% yield. 1H NMR (400MHz, CDCl3) δ 4.00 (q, J=7.1Hz, 4H), 3.74 (q, J=7.1Hz, 4H), 1.39-1.26 (m, 12H). HRMS (EI) m/z calcd C10H20N2S3 [M]+ 264.0789, found 264.0784. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 843 mg | With 1,4-diaza-bicyclo[2.2.2]octane In tetrahydrofuran at 20℃; for 16h; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 50% | With 1,4-diaza-bicyclo[2.2.2]octane In tetrahydrofuran at 20℃; for 16h; |