[ CAS No. 1950-85-2 ]

Name: 1950-85-2|Sodium methanesulfonothioate|97%
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Product Details of [ 1950-85-2 ]

CAS No. :	1950-85-2	MDL No. :	MFCD03425630
Formula :	CH₃NaO₂S₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	134.15 g/mol	Pubchem ID :	23688755
Synonyms :

Safety of [ 1950-85-2 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 1950-85-2 ]

Upstream synthesis route of [ 1950-85-2 ]
Downstream synthetic route of [ 1950-85-2 ]

[ 1950-85-2 ] Synthesis Path-Upstream 1~3

1
[ 20277-69-4 ]
[ 1950-85-2 ]

Yield	Reaction Conditions	Operation in experiment
77%	With sulfur In methanol for 0.333333 h; Heating / reflux	A mixture of sodium methanesulfinate (5.43 g, 53 mmol) and sulphur (1.666 g, 52 mmol) in dry methanol (310 ml) was heated to reflux for 20 min, at which time almost all of the sulphur had dissolved. The hot solution was filtered and the filtrate concentrated to dryness. The off-white solid was stirred with a small amount of dry ethanol 0 at room temperature, filtered and concentrated. The trituration was repeated until ¹H NMR of the white residue showed no more traces of sodium methanethiosulfonate. The filtrates were then combined and evaporated to dryness to yield the title compound (5.40 g, 77percent) as fine EPO <DP n="41"/>white needles; mp 271-272⁰C (lit.[G.L. Kenyon, T. W. Bruice, Methods Enzymol. 1977, 47, 407-430.] 272-273.5⁰C); ¹H NMR (200 MHz, CDCl₃) δ 3.18 (s, 3H, CH₃); anal, calculated, for CH₃NaO₂S₂: C 8.95, H 2.25; found: C 8.86, H 2.55.; Improved Synthesis for NaMTS EPO <DP n="40"/>[0136] An alternative preparation of NaMTS (J.D. Macke, L. Field, /. Org. Chem. 1988, 53, 396-402) has been successfully tested, which is faster and avoids the tedious and lengthy separation of by-product from NaMTS as required in the Na₂SZMe₃SiCl method. NaMTS was synthesized in high yield by refluxing sodium sulfinate with sulphur in methanol s (Scheme 16, Fig. 19), described in further detail below). Although formation of small amounts of an unknown by-product was observed, it could be easily separated from NaMTS.

Reference： [1] Chemistry Letters, 1987, p. 2161 - 2162
[2] Patent: WO2006/55437, 2006, A2, . Location in patent: Page/Page column 38; 39; sheet 23
[3] Journal of Organic Chemistry, 2005, vol. 70, # 24, p. 9740 - 9754
[4] Dalton Transactions, 2011, vol. 40, # 45, p. 12310 - 12319
[5] Journal of Organic Chemistry, 1988, vol. 53, # 2, p. 396 - 402

2
[ 124-63-0 ]
[ 1950-85-2 ]

Reference： [1] Journal of Organic Chemistry, 2005, vol. 70, # 24, p. 9740 - 9754
[2] Chemical Communications, 2007, # 30, p. 3145 - 3147
[3] Synthetic Communications, 2008, vol. 38, # 21, p. 3726 - 3750
[4] Patent: WO2006/134489, 2006, A1, . Location in patent: Page/Page column 15-17
[5] Patent: EP1832575, 2007, A1, . Location in patent: Page/Page column 3-4
[6] Patent: EP1980559, 2008, A1, . Location in patent: Page/Page column 9-10
[7] Carbohydrate Research, 2009, vol. 344, # 13, p. 1758 - 1763
[8] Patent: US2010/168216, 2010, A1, . Location in patent: Page/Page column 4
[9] Patent: EP1939186, 2008, A1, . Location in patent: Page/Page column 6
[10] Patent: WO2008/146105, 2008, A1, . Location in patent: Page/Page column 20-23

3
[ 2386-57-4 ]
[ 1950-85-2 ]

Reference： [1] Patent: US2009/275721, 2009, A1,

[ 1950-85-2 ] Synthesis Path-Downstream 1~25

1
[ 1647-23-0 ]
[ 1950-85-2 ]
methanethiosulfonic acid <i>S</i>-(3,3-dimethyl-butyl) ester [ No CAS ]

Reference： [1]Chemistry - A European Journal,2002,vol. 8,p. 4129 - 4137

2
[ 74-96-4 ]
[ 1950-85-2 ]
[ 2043-76-7 ]

Reference： [1]Journal of Organic Chemistry,2005,vol. 70,p. 9740 - 9754

3
[ 4196-35-4 ]
[ 1950-85-2 ]
2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl methanethiosulfonate [ No CAS ]
[ 329365-81-3 ]

Reference： [1]Journal of Organic Chemistry,2005,vol. 70,p. 9740 - 9754

4
[ 53081-30-4 ]
[ 1950-85-2 ]
2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl methanethiosulfonate [ No CAS ]
2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl methanethiosulfonate [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2005,vol. 70,p. 9740 - 9754

5
[ 124-63-0 ]
[ 1950-85-2 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium sulfide; In ethanol; at -15℃;	EXAMPLE 4; Synthesis of (Z) -5-Fluoro-2-methyl-1- [ [4- (methylsulfinyl) phenyl] methylene] -IH-indene-3 -acetic acid 2-methanesulfonylsulfanylethyl ester; Sodium sulphide nonahydrate (4 g; 16.32 mmol) is EPO <DP n="17"/>suspended in 12 ml of anhydrous ethanol at -150C. To this suspension is added dropwise a solution of methansolfochloride (1.4 ml, 17.96 mmol) in 3.2 ml of anhydrous ethanol . After complete addition the suspension is kept overnight under stirring. The mixture of reaction is filtered and the solution evaporated to dryness.Pure sodium methanthiosulfonate is obtained after crystallization of the residue by ethanol. The sodium methanthiosulfonate (690 mg, 5.14 mmol) is suspended in ethanol and 2-bromoethanol (0.76 ml, 10.28 mmol) is then added dropwise to the suspension. After the complete addition the reaction mixture is refluxed for 7 hours . After cooling, the product is filtered to remove NaBr. The ethanol solution is evaporated, and the residue is dissolved in CHCl3 and extracted with water. The aqueous solution is evaporated to dryness, tetrahydrofuran (THF) is added to the residue and the obtained suspension is filtered.The THF solution is evaporated to obtain a pale yellowish oil (methanethiosulfonic acid S- (2- hydroxyethyl) ester, HEMTS) . HEMTS (400 mg, 2.56 mmol), sulindac sulfone (912 mg, 2.56 mmol) and dimethylaminopyridine (DMAP) (15 mg) are added to a IN solution of EPO <DP n="18"/>dicyclohexhylcarbodiimide (DCC) in methylene chloride (2.6 ml) . The reaction is stirred at room temperature, under nitrogen for 1.5 hours. The mixture is filtered, and the dichloromethane solution is extracted with IN HCl, water, saturated solution of sodium bicarbonate and water. After evaporation of the solvent the residue was chromatographed on a silica gel column, eluting with dichloromethane containing 0.5% of methanol. The compound has a melting point of 118.5-119.5 0C.
	With sodium sulfide; In ethanol; at -15 - 20℃; for 12h;	EXAMPLE 1. Synthesis of methanethiosulfonic acid S-(2-hydroxyethyl) ester. A solution of CH3SO2Cl (5.9 g) in ethanol (9.2 ml) is added dropwise to a refrigerated (-15C) solution of Na2S (46.98 mmol) in ethanol(34.5 ml). The reaction mixture is stirred at room temperature for 12 hours. After filtration and crystallization from ethanol, sodium methanthiosulfonate, as a white solid is obtained. The sodium methanthiosulfonate (2.5 g; 18.64 mmol) is dissolved in 30 ml of ethanol and a solution of 2-bromoethanol (2.6 ml; 37.28 mmol) in ethanol (6 ml) is added dropwise. The solution is heated at 100 C for 8 hours under nitrogen. The mixture is filtered, the solution is evaporated to dryness and the residue is dissolved in CHCl3 and extracted with water. The aqueous solution is evaporated to dryness, tetrahydrofuran (THF) is added to the residue and the obtained suspension is filtered. The THF solution is evaporated and methanethiosulfonic acid S-(2-hydroxyethyl) ester as an oily yellow product is obtained.
	With sodium sulfide; In ethanol; at -15 - 20℃; for 12h;	EXAMPLE 3. Synthesis of 2-butyl-4-chloro-1-[(2'-(1H-tetrazol-5-yl)(1,1-biphenyl)-4-yl)methyl]-1H-imidazole-5-carboxylic acid 2-(methylsulfonylthio)-ethyl ester; Step 1: Synthesis of methanethiosulfonic acid S-(2-hydroxyethyl) ester; A solution of CH3SO2Cl (5.9 g) in ethanol (9.2 ml) is added dropwise to a refrigerated (-15C) solution of Na2S (46.98 mmol) in ethanol(34.5 ml). The reaction mixture is stirred at room temperature for 12 hours. After filtration and crystallization from ethanol, sodium methanthiosulfonate, as a white solid is obtained. The sodium methanthiosulfonate (2.5 g; 18.64 mmol) is dissolved in 30 ml of ethanol and a solution of 2-bromoethanol (2.6 ml; 37.28 mmol) in ethanol (6 ml) is added dropwise. The solution is heated at 100 C for 8 hours under nitrogen. The mixture is filtered, the solution is evaporated to dryness and the residue is dissolved in CHCl3 and extracted with water. The aqueous solution is evaporated to dryness, tetrahydrofuran (THF) is added to the residue and the obtained suspension is filtered. The THF solution is evaporated and methanethiosulfonic acid S-(2-hydroxyethyl) ester as an oily yellow product is obtained.

	With sodium sulfide; In ethanol; at -15 - 20℃;	A solution of CH3SO2Cl (5.9 g) in ethanol (9.2 ml) is added dropwise to a refrigerated (-15 C.) solution of Na2S (46.98 mmol) in ethanol (34.5 ml).The reaction mixture is stirred at room temperature for 12 hours. After filtration and crystallization from ethanol, sodium methanthiosulfonate, as a white solid, is obtained. The sodium methanthiosulfonate (2.5 g; 18.64 mmol) is dissolved in 30 ml of ethanol and a solution of 2-bromoethanol (2.6 ml; 37.28 mmol) in ethanol (6 ml) is added dropwise. The solution is heated at 100 C. for 8 hours under nitrogen. The mixture is filtered, the solution is evaporated to dryness and the residue is dissolved in CHCl3 and extracted with water.The aqueous solution is evaporated to dryness, tetrahydrofuran (THF) is added to the residue and the obtained suspension is filtered. The THF solution is evaporated and methanethiosulfonic acid S-(2-hydroxyethyl)ester, as an oily yellow product, is obtained.
	With sodium sulfide; In ethanol; at -15 - 20℃; for 12h;	EXAMPLE 4. Synthesis of 2-(methylsulfonylthio)ethyl 2-(5-fluoro-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-1-carboxamido)acetate. Step 1: Synthesis of methanethiosulfonic acid S-(2-hydroxyethyl) ester.; A solution of CH3SO2Cl (5.9 g) in ethanol (9.2 ml) is added dropwise to a refrigerated (-15C) solution of Na2S (46.98 mmol) in ethanol(34.5 ml). The reaction mixture is stirred at room temperature for 12 hours. After filtration and crystallization from ethanol, sodium methanthiosulfonate, as a white solid is obtained. The sodium methanthiosulfonate (2.5 g; 18.64 mmol) is dissolved in 30 ml of ethanol and a solution of 2-bromoethanol (2.6 ml; 37.28 mmol) in ethanol (6 ml) is added dropwise. The solution is heated at 100 C for 8 hours under nitrogen. The mixture is filtered, the solution is evaporated to dryness and the residue is dissolved in CHCl3 and extracted with water. The aqueous solution is evaporated to dryness, tetrahydrofuran (THF) is added to the residue and the obtained suspension is filtered. The THF solution is evaporated and methanethiosulfonic acid S-(2-hydroxyethyl) ester as an oily yellow product is obtained.
	With sodium sulfide; In ethanol; at -15 - 20℃; for 12h;Product distribution / selectivity;	EXAMPLE 3. Synthesis of (llalpha, 13E, 15S) -11, 15- dihydroxy-9-oxoprost-13-en-l-oic acid 2- (methylsulfonylthio) ethyl ester. Step 1: Synthesis of methanethiosulfonic acid S- (2- hydroxyethyl ) ester.; A solution of CH3SO2Cl (5.9 g) in ethanol (9.2 ml) is added dropwise to a refrigerated (-150C) solution of Na2S (46.98 mmol) in ethanol(34.5 ml). The reaction mixture is stirred at room temperature for 12 hours. After filtration and crystallization from ethanol, sodium methanthiosulfonate, as a white solid, is obtained. The sodium methanthiosulfonate (2.5 g; 18.64 mmol) is dissolved in 30 ml of ethanol and a solution of 2-bromoethanol (2.6 ml; 37.28 mmol) in ethanol (6 ml) is added dropwise. The solution is heated at 100C for 8 hours under nitrogen. The mixture is filtered, the solution is evaporated to dryness and the residue is dissolved in CHCl3 and <n="22"/>extracted with water.The aqueous solution is evaporated to dryness, tetrahydrofuran (THF) is added to the residue and the obtained suspension is filtered. The THF solution is evaporated and methanethiosulfonic acid S- (2 - hydroxyethyl ) ester, as an oily yellow product, is obtained.; EXAMPLE 5. Synthesis of (llalpha, 13E,15S) -11, 15- dihydroxy-9-oxoprost-13-en-l-oic acid 2- (methylsulfonylthio) ethylamide. Step 1: Synthesis of S- (2-aminoethyl) methan- thiosulfonateA solution of CH3SO2Cl (5.9 g) in ethanol (9.2 ml) is added dropwise to a refrigerated (-150C) solution of Na2S (46.98 mmol) in ethanol(34.5 ml). The reaction mixture is stirred at room temperature for 12 hours. After filtration and crystallization from ethanol, sodium methanthiosulfonate, as a white solid, is obtained.The sodium methanthiosulfonate (1.20 g; 8.9 mmol) is dissolved in 17 ml of ethanol and 2-bromoethylamine <n="24"/>hydrobromide (1.8 g,- 8.9 mmol) is added. The solution is heated at 1000C for 5 hours under nitrogen. At the end of the reaction the mixture is cooled at O0C filtered to remove NaBr, and the solution is evaporated to obtain an oil that after treatment with ethanol crystallizes and gives a compound with a melting point of 112.0-112.8 0C.

Reference： [1]Journal of Organic Chemistry,2005,vol. 70,p. 9740 - 9754
[2]Synthetic Communications,2008,vol. 38,p. 3726 - 3750
[3]Patent: WO2006/134489,2006,A1 .Location in patent: Page/Page column 15-17
[4]Patent: EP1832575,2007,A1 .Location in patent: Page/Page column 3-4
[5]Patent: EP1980559,2008,A1 .Location in patent: Page/Page column 9-10
[6]Carbohydrate Research,2009,vol. 344,p. 1758 - 1763
[7]Patent: US2010/168216,2010,A1 .Location in patent: Page/Page column 4
[8]Patent: EP1939186,2008,A1 .Location in patent: Page/Page column 6
[9]Patent: WO2008/146105,2008,A1 .Location in patent: Page/Page column 20-23

6
[ 1950-85-2 ]
[ 3068-32-4 ]
[ 398469-69-7 ]

Yield	Reaction Conditions	Operation in experiment
67%	With tetra-(n-butyl)ammonium iodide; In toluene; for 1.25h;Heating / reflux;	Acetobromogalactose 1 (1.1 g, 2.68 mmol) and sodium o methanethiosulfonate (0.45 g, 3.35 mmol) in toluene (50 mL) were concentrated in vacuo to approximately 30 mL to remove any water as the azeotrope. The mixture was made up to 50 mL with more toluene and again concentrated to 30 mL. A catalytic amount of tetrabutylammonium iodide was added and the mixture heated at reflux for 75 minutes. After cooling, Celite (to stop the formation of a salt cake on top of the column) was added and the s whole mixture loaded directly on to a flash silica column. Elution with 40% ethyl acetate in petroleum ether and recrystallization from petroleum ether/ethyl acetate gave the title compound (787 mg, 67%) as colorless prisms; mp 118-119C (petroleum ether/ethyl acetate);[alpha]2D3 = + 8.5 (c 1.0, CHCl3); IR (KBr) 1753 (C=O), 1325, 1138 (S-SO2) crn 1; 1H NMR (400MHz, CDCl3) delta 1.99 (s, 3H, Ac), 2.05 (s, 3H, Ac), 2.08 (s, 3H, Ac), 2.17 (s, 3H, Ac), 3.43 (s, o 3H, CH3SO2-), 4.05 (ddd, / 7.4, 4.2, 0.9 Hz, IH), 4.08 (dd, J 18.3, 7.5 Hz, IH), 4.20 (dd, J10.8, 4.3 Hz, IH), 5.13 (dtd, J 10.7, 7.6, 3.4 Hz, IH), 5.26 (s, IH), 5.27 (dd, / 14.8, 10.3 Hz,IH), 5.48 (dd, / 3.4, 0.8 Hz, IH); 13C NMR (100 MHz, CDCl3) delta 20.5, 20.6, 20.6, 20.6 (4 x EPO <DP n="29"/>CH3CO), 52.7 (CH3SO2-), 61.8 (C-6), 65.8, 67.0, 71.3, 75.3, 87.0 (1J1CH 165 Hz, C-I), 169.7, 169.7, 170.0, 170.2 (4 x C=O); HRMS m/z (ES): found 460.0951; C15H26NO11S2 requires 460.0947.

Reference： [1]Canadian Journal of Chemistry,2005,vol. 83,p. 929 - 936
[2]Journal of Organic Chemistry,2005,vol. 70,p. 9740 - 9754
[3]Patent: WO2006/55437,2006,A2 .Location in patent: Page/Page column 25-27; sheet 8

7
[ 879096-66-9 ]
[ 1950-85-2 ]
3-methanethiosulfonylmethyl-1-oxyl-4-(pyren-1-yl)-2,2,5,5-tetramethyl-2,5-dihydro-1H-pyrrole radical [ No CAS ]

Reference： [1]Journal of Heterocyclic Chemistry,2006,vol. 43,p. 81 - 86

8
[ 879096-67-0 ]
[ 1950-85-2 ]
3-methanethiosulfonylmethyl-1-methanesulfonyl-4-(pyren-1-yl)-2,2,5,5-tetramethyl-2,5-dihydro-1H-pyrrole [ No CAS ]

Reference： [1]Journal of Heterocyclic Chemistry,2006,vol. 43,p. 81 - 86

9
[ 874620-28-7 ]
[ 1950-85-2 ]
C₂₀H₃₈N₃O₇S₄ [ No CAS ]

Reference： [1]Chemical Communications,2005,p. 1880 - 1882

10
[ 852289-10-2 ]
[ 1950-85-2 ]
C₂₀H₃₈N₃O₇S₄ [ No CAS ]

Reference： [1]Chemical Communications,2005,p. 1880 - 1882

11
[ 898550-04-4 ]
[ 1950-85-2 ]
S-(2,4,6-trimethylpyridin-3-yl)methyl methanesulfothiolate [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2006,vol. 45,p. 3126 - 3130

12
methylamino-acetic acid 2-bromo-ethyl ester hydrochloride [ No CAS ]
[ 1950-85-2 ]
methylamino-acetic acid 2-methanesulfonylsulfanyl-ethyl ester hydrochloride [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2006,vol. 45,p. 3126 - 3130

13
dimethylamino-acetic acid 2-bromo-ethyl ester hydrochloride [ No CAS ]
[ 1950-85-2 ]
dimethylamino-acetic acid 2-methanesulfonylsulfanyl-ethyl ester hydrochloride [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2006,vol. 45,p. 3126 - 3130

14
[ 886546-77-6 ]
[ 1950-85-2 ]
4-(4-benzoylphenyl)-3-methanethiosulfonylmethyl-2,2,5,5-tetramethyl-2,5-dihydro-1H-pyrrol-1-yloxyl radical [ No CAS ]

Reference： [1]Synthesis,2006,p. 439 - 446

15
4,4-difluoro-8-iodomethyl-1,3,5,7-tetramethyl-2,6-diethyl-4-bora-3a,4a-diaza-s-indacene [ No CAS ]
[ 1950-85-2 ]
4,4-difluoro-8-methanesulfonylmethyl-1,3,5,7-tetramethyl-2,6-diethyl-4-bora-3a,4a-diaza-s-indacene [ No CAS ]

Reference： [1]Tetrahedron,2006,vol. 62,p. 10352 - 10360

16
3-bromomethyl-2,2,5,5-tetramethyl-4-[(4,4-di-fluoro-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s-indacene-8-phenyl-4'-oxy)-ylmethyl]-2,5-dihydro-1H-pyrrol-1-yloxyl radical [ No CAS ]
[ 1950-85-2 ]
3-methanethiosulfonylmethyl-2,2,5,5-tetramethyl-4-[(4,4-difluoro-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s-indacene-8-phenyl-4'-oxy)ylmethyl]-2,5-dihydro-1H-pyrrol-1-yloxyl radical [ No CAS ]

Reference： [1]Tetrahedron,2006,vol. 62,p. 10352 - 10360

17
[ 1950-85-2 ]
[ 71283-21-1 ]
amino-acetic acid 2-methanesulfonylsulfanyl-ethyl ester hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70 - 90%	In DMF (N,N-dimethyl-formamide); at 70℃; for 4h;	The schematic presentation of the compound synthesis is given in Figure 4. In the first reaction glycine or its N alkylated derivative (1) in the form of the free compound or as a HCl salt (20 mmol) was suspended in 2-bromoethanol (14.3 ml, 200mmol) and cooled to 0C. Thionyl chloride (1.8 ml, 25 mmol) was added dropwise and reaction mixture was stirred at room temperature until a clear solution was obtained. Resulting solution was poured into 200 ml of ether, precipitated solid was filtered, washed with ether and dried in vacuo. In the case that only oil separates instead of precipitate, ether was decanted; oil was washed with ether (2x 100ml) and all the residual solvents were removed in vacuo. Oil usually solidifies upon standing overnight at 4C. Compound bromo-ethyl ester of glycine or its N alkylated derivative (2), was obtained as HCl salt. In the second reaction the salt of 2-bromo-ethyl ester of glycine or its N alkylated derivative (2) (10 mmol) was dissolved in DMF (10 ml) and <strong>[1950-85-2]sodium methanethiosulfonate</strong> (1.47g, 11 mmol) was added. Mixture was heated at 70C for 4 hours, solid precipitate was filtered out and DMF was evaporated in vacuo. The residue was dissolved in small amount of boiling acetonitrile (20 ml), filtered and filtrate evaporated in vacuo. Product, 2-methanesulfonylsulfanyl-ethyl ester of glycine or its N alkylated derivative (3), is also obtained as HCl salt. Solid products can be recrystallized from acetonitrile-ether or ethanol-ether.Results and Discussion The yield of the first synthesis reaction was over 95%, and the purity of the compound, 2-bromo-ethyl ester of glycine or its N alkylated derivative (2), was over 98%. The yield of the second reaction was 70 - 90%. The resulted compound, 2-methanesulfonylsulfanyl-ethyl ester of glycine or its N alkylated derivative (3), may contain small amount <5% NaCl.

Reference： [1]Patent: EP1535903,2005,A1 .Location in patent: Page/Page column 6-7; 14
[2]Angewandte Chemie - International Edition,2006,vol. 45,p. 3126 - 3130

18
[ 110-81-6 ]
[ 1950-85-2 ]
[ 2043-76-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2007,vol. 15,p. 2453 - 2467

19
[ 5943-30-6 ]
[ 1950-85-2 ]
S-sec-butyl methanethiosulfonate [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2007,vol. 15,p. 2453 - 2467

20
[ 912457-77-3 ]
[ 1950-85-2 ]
5,5-dimethyl-2,2-bis(2-methanethiosulfonylethoxymethyl)pyrrolidin-1-yloxyl [ No CAS ]

Reference： [1]Chemistry Letters,2006,vol. 35,p. 834 - 835

21
[ 1950-85-2 ]
[ 13204-56-3 ]
[ 871010-56-9 ]

Reference： [1]Australian Journal of Chemistry,2005,vol. 58,p. 188 - 198

22
acetic acid 3,5-diacetoxy-2-acetylsulfanylmethyl-6-bromo-tetrahydro-pyran-4-yl ester [ No CAS ]
[ 1950-85-2 ]
[ 871010-82-1 ]

Reference： [1]Australian Journal of Chemistry,2005,vol. 58,p. 188 - 198

23
[ 590-92-1 ]
[ 1950-85-2 ]
[ 92953-12-3 ]

Yield	Reaction Conditions	Operation in experiment
	In N,N-dimethyl-formamide; at 60℃; for 4h;	EXAMPLE 2. Synthesis of 3-methanesulfonylsulfanyl-propionic acid. Sodium methanthiosulfonate (1.5 g; 11.18 mmol) and 3-<strong>[590-92-1]bromopropionic acid</strong> (900 mg; 5.88 mmol) 97% are dissolved in dimethylformamide (DMF, 9.05 ml). The reaction is performed at 60 C, stirring under nitrogen for 4 hours. The solution is evaporated to dryness and the residue is dissolved in water, acidified with 10 ml of a 2N KHSO4 and washed with ethyl acetate. The organic phase is extracted with cold 2N KHSO4, then with brine and finally dried on anhydrous sodium sulphate and evaporated to dryness. An oily yellow product is obtained.
		EXAMPLE 4: Synthesis of 3-(methanesulfonylsulfanyl)-propionic acid 2-butyl-4-chloro-1-[p-(o-1H-tetrazol-5-ylphenyl)-benzyl]imidazole-5-methyl ester; Step 1: Synthesis of 3-methanesulfonylsulfanyl-propionic acid; Sodium methanthiosulfonate (1.5 g; 11.18 mmol) and 3-<strong>[590-92-1]bromopropionic acid</strong> (900 mg; 5.88 mmol) 97% are dissolved in dimethylformamide (DMF, 9.05 ml). The reaction is performed at 60 C, stirring under nitrogen for 4 hours. The solution is evaporated to dryness and the residue is dissolved in water, acidified with 10 ml of a 2N KHSO4 and washed with ethyl acetate. The organic phase is extracted with cold 2N KHSO4, then with brine and finally dried on anhydrous sodium sulphate and evaporated to dryness. An oily yellow product is obtained.
		Sodium methanethiosulfonate (1.5 g; 11.18 mmol) and 3- <strong>[590-92-1]bromopropionic acid</strong> (900 mg; 5.88 mmol) 97% are dissolved in dimethylformamide (DMF, 9.05 ml) . The reaction is performed at 60 C, stirring under nitrogen for 4 hours. The solution is evaporated to dryness and the residue is dissolved in water, acidified with 10 ml of a 2N KHSO4 solution and washed with ethyl acetate. The organic phase is extracted with cold 2N KHSO4 solution, then with ice water and finally dried on anhydrous sodium sulphate and evaporated to dryness . An oily yellow product is obtained.

In N,N-dimethyl-formamide; at 60℃; for 4h;

EXAMPLE 1. Synthesis of (5-fluoro-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methyl 3-(methylsulfonyl thio)propanoate.; Step 1: Preparation of 3-methanesulfonylsulfanyl-propionic acid. Sodium methanthiosulfonate (1.5 g; 11.18 mmol) and 3-<strong>[590-92-1]bromopropionic acid</strong> (900 mg; 5.88 mmol) 97% are dissolved in dimethylformamide (DMF, 9.05 ml). The reaction is performed at 60 C, stirring under nitrogen for 4 hours. The solution is evaporated to dryness and the residue is dissolved in water, acidified with 10 ml of a 2N KHSO4 and washed with ethyl acetate. The organic phase is extracted with cold 2N KHSO4, then with brine and finally dried on anhydrous sodium sulphate and evaporated to dryness to obtain an oily yellow product.

Reference： [1]Patent: EP1832575,2007,A1 .Location in patent: Page/Page column 4
[2]Patent: EP1980559,2008,A1 .Location in patent: Page/Page column 10
[3]Patent: WO2009/109501,2009,A2 .Location in patent: Page/Page column 25
[4]Patent: EP1939186,2008,A1 .Location in patent: Page/Page column 5

24
[ 57602-02-5 ]
[ 1950-85-2 ]
[ 212262-00-5 ]
[ 212262-08-3 ]

Yield	Reaction Conditions	Operation in experiment
	In N,N-dimethyl-formamide; at 20℃; for 72h;	1,14-dibramo-3,6,9,12-tetraoxatetradecane (3.35 g, 9.2 mmol) and sodium methanethiosulfonate (2.48 g, 18.5 mmol) were dissolved in dry DMF (40 mL) and stirred at room temperature for 3 days. The solvent was evaporated. The residue was purified by column chromatography on SiO2. Elution with ethyl acetate/hexane (9:1) afforded, after evaporation, 1-(14-bromo-3,6,9,12-tetraoxatetradecyl) methanethiosulfonate (0.85 g) as a pale yellow oil and tetraoxatetradecane-1,14-diyl-bis-methanethiosulfonate (useful as a cross linker) as a slightly yellow colored oil (1.64 g).

Reference： [1]Patent: EP966304,2005,B1 .Location in patent: Page/Page column 17

25
[ 1450754-38-7 ]
[ 1950-85-2 ]
C₈H₁₂N₂O₂S₂ [ No CAS ]

Reference： [1]RSC Advances,2019,vol. 9,p. 7610 - 7614

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[ CAS No. 1950-85-2 ]

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Application In Synthesis of [ 1950-85-2 ]

[ 1950-85-2 ] Synthesis Path-Upstream 1~3

[ 1950-85-2 ] Synthesis Path-Downstream 1~25

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