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Chemistry
Heterocyclic Building Blocks
Thiazoles
2-(Chloromethyl)-4-methylthiazole
Chemistry
Heterocyclic Building Blocks
Organic Building Blocks
Thiazoles
Chlorides

[ CAS No. 50398-72-6 ] {[proInfo.proName]}

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Chemical Structure| 50398-72-6
Chemical Structure| 50398-72-6
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Product Details of [ 50398-72-6 ]

CAS No. :50398-72-6 MDL No. :MFCD08060046
Formula : C5H6ClNS Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 147.63 Pubchem ID :-
Synonyms :

Safety of [ 50398-72-6 ]

Signal Word: Class:
Precautionary Statements: UN#:
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Application In Synthesis of [ 50398-72-6 ]

* 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 [ 50398-72-6 ]

[ 50398-72-6 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 13750-63-5 ]
  • [ 50398-72-6 ]
YieldReaction ConditionsOperation in experiment
88.3% With thionyl chloride; In dichloromethane; at 0 - 20℃; for 1h; To a stirred solution <strong>[13750-63-5](4-methylthiazol-2-yl)methanol</strong> (2, 1 g, 7.7 mmol) in DCM (20 mL), was added SOCl2(0.89 mL, 11.55 mmol) drop wise at 0 C and the reaction mixture was stirred at rt for 1 h (Reaction condition b). The reaction mixture was evaporated under vacuum and dried to afford the product as brown oil (3) (1 g, 88.3 %, Yield). NMR (400 MHz, CDC13) delta (ppm): 6.91 (s, 1H), 4.82 (s, 2H), 2.45 (s, 3H).
73% With methanesulfonyl chloride; triethylamine; In dichloromethane; at 20℃;Inert atmosphere; A 25-mL round bottom flask equipped with a magnetic stirrer under nitrogen was charged with alcohol 21a (210 mg, 1.67 mmol), CH2Cl2 (4 mL), and triethylamine (0.45 mL, 3.25 mmol). Methanesulfonyl chloride (0.25 mL, 3.2 mmol) was added via a syringe over 5 minutes. The resulting reaction mixture was stirred at room temperature overnight. The reaction mixture was diluted with CH2Cl2 (30 mL) and washed with saturated NaHCO3 (15 ml), dried over Na2SO4, and concentrated under reduced pressure and purified on an ISCO using a maximum gradient of 5% MeOH/DCM affording desired compound (180 mg, 73% yield). 1H NMR (CDCl3, 300 MHz) delta: 6.94 (s, 1H), 4.84 (s, 2H), 2.47 (s, 3H).
56% To a 0 C solution of (4-methyl-l,3-thiazol-2-yl)methanol (1.70 g, 14.4 mmol) in dichloromethane (25 mL) was added thionyl chloride (2.55 g, 21.6 mmol) dropwise, after which the reaction mixture was allowed to warm up to room temperature and stirred at that temperature for two hours. The reaction mixture was washed by the addition of saturated sodium bicarbonate solution (1 x 40 mL), and the organic layer was separated, dried (sodium sulfate), filtered and concentrated to a residue. Purification was achieved by silica gel chromatography using 20% ethyl acetate in hexanes to afford 2-(chloromethyl)-4-methyl-l,3- thiazole (1.20 g, 8.12 mmol, 56% yield) as pale yellow viscous oil. 1H NMR (300 MHz, CDC13) delta (ppm): 6.87 (s, 1H), 4.76 (s, 2H), 2.40 (s, 3H).
With thionyl chloride; In dichloromethane; at 0℃; for 2h; The compound (142 mg) prepared in step 1), and thionyl chloride (1 mL) were added to dichloromethane (3 mL), and stirred at 0C for 2 hrs. The solution was warmed to room temperature, filtered in a vacuum, and subjected to azeotropic distillation with toluene. The distillate was used in a subsequent reaction without purification.
With thionyl chloride; In dichloromethane; at 0 - 20℃; for 2h; Step 2 Synthesis of 2-(chloromethyl)-4-methylthiazole To a solution of <strong>[13750-63-5](4-methylthiazol-2-yl)methanol</strong> (0.5 g, 3.87 mmol) in DCM (5 mL) was added thionyl chloride (0.19 ml, 2.6 mmol) at 0 C. The mixture was stirred at room temperature for 2 hour. The reaction was concentrated to give 2-(chloromethyl)-4-methylthiazole (570 mg, crude) as yellow oil, which was used without purification. LCMS retention time 0.895 min; LCMS MH+ 148
With thionyl chloride; In dichloromethane; at 0 - 20℃; for 2h; To a solution of <strong>[13750-63-5](4-methylthiazol-2-yl)methanol</strong> (0.5 g, 3.87 mmol) in DCM (5 mL) was added thionyl chloride (0.19 ml, 2.6 mmol) at 0 C. The mixture was stirred at room temperature for 2 hour. The reaction was concentrated to give 2-(chloromethyl)thiazole (570 mg, crude) as yellow oil, which was used without purification. LCMS retention time 0.895 min; LCMS MH+ 148
1 g With thionyl chloride; In dichloromethane; at 0 - 20℃; for 1h; To a stirred solution of <strong>[13750-63-5](4-methylthiazol-2-yl)methanol</strong> (2, 0.9 g, 6.97 mmol) in DCM (5 mL), was added SOCl2 (0.83 mL, 11 mmol) drop wise at 0 C and the reaction mixture was stirred at room temperature for 1 h. The reaction mixture was neutralized using cold NaHC03 (5 mL) solution and extracted with DCM (2 X 25 mL). Organic layer was washed with brine (5mL) solution, dried over anhydrous Na2S04 and evaporated to afford the product as yellow oil. (1 g). MS (ESI): mass calcd.for C5H6CINS , 146.99; m/z found 148.1 (M+H)+.

Reference： [1]Patent: WO2019/77631,2019,A1 .Location in patent: Paragraph 000133; 000331
[2]Patent: WO2013/142712,2013,A1 .Location in patent: Page/Page column 68
[3]Patent: WO2012/88431,2012,A1 .Location in patent: Page/Page column 109
[4]Journal of the Chemical Society,1949,p. Spl. 113
[5]Tetrahedron,2003,vol. 59,p. 1381 - 1387
[6]Patent: WO2014/3483,2014,A1 .Location in patent: Page/Page column 46
[7]Patent: WO2014/143799,2014,A2 .Location in patent: Page/Page column 412; 413
[8]Patent: US2014/275528,2014,A1 .Location in patent: Paragraph 0357; 0358
[9]Patent: WO2019/58393,2019,A1 .Location in patent: Paragraph 000368
  • 2
  • [ 13750-68-0 ]
  • [ 50398-72-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: reducing agent 2: chlorinating agent
Multi-step reaction with 2 steps 1: sodium tetrahydroborate; methanol / 2 h / 0 - 20 °C 2: thionyl chloride / dichloromethane / 2 h / 0 - 20 °C
Multi-step reaction with 2 steps 1: sodium tetrahydroborate / ethanol / 1 h / 20 °C 2: triethylamine; methanesulfonyl chloride / dichloromethane / 20 °C / Inert atmosphere
Multi-step reaction with 2 steps 1: sodium tetrahydroborate; methanol / 1 h / -60 °C / Inert atmosphere 2: thionyl chloride / dichloromethane / 2 h / 0 - 20 °C
Multi-step reaction with 2 steps 1: sodium tetrahydroborate / methanol / 1 h / -60 °C 2: thionyl chloride / dichloromethane / 2 h / 0 - 20 °C
Multi-step reaction with 2 steps 1: sodium tetrahydroborate; methanol / 2 h / 0 - 20 °C 2: thionyl chloride / dichloromethane / 1 h / 0 - 20 °C
Multi-step reaction with 2 steps 1: methanol; sodium tetrahydroborate / 1 h / 0 - 20 °C 2: thionyl chloride / dichloromethane / 1 h / 0 - 20 °C

Reference： [1]Bona, Fabio; De Vitis, Luisella; Florio, Saverio; Ronzini, Ludovico; Troisi, Luigino [Tetrahedron, 2003, vol. 59, # 9, p. 1381 - 1387]
[2]Current Patent Assignee: IRONWOOD PHARMACEUTICALS INC - WO2012/88431, 2012, A1
[3]Current Patent Assignee: RUTGERS, THE STATE UNIVERSITY OF NEW JERSEY - WO2013/142712, 2013, A1
[4]Current Patent Assignee: HYDRA BIOSCIENCES, INC - WO2014/143799, 2014, A2
[5]Current Patent Assignee: HYDRA BIOSCIENCES, INC - US2014/275528, 2014, A1
[6]Current Patent Assignee: JUBILANT PHARMOVA LTD - WO2019/58393, 2019, A1
[7]Current Patent Assignee: JUBILANT PHARMOVA LTD - WO2019/77631, 2019, A1
  • 3
  • [ 50398-72-6 ]
  • [ 13750-63-5 ]
  • [ 156-57-0 ]
  • [ 10191-60-3 ]
  • N-cyano-N'-{2-[(4-methylthiazol-2-yl)methylthio]ethyl}-S-methylisothiourea [ No CAS ]
YieldReaction ConditionsOperation in experiment
With thionyl chloride; EXAMPLE 16 When 2-chloromethyl-4-methylthiazole [prepared from 2-hydroxymethyl-4-methylthiazole and thionyl chloride] is reacted with cysteamine hydrochloride and about two equivalents of a strong base such as sodium methoxide and the resultant amine treated with dimethyl cyanodithioimidocarbonate there is produced N-cyano-N'-{2-[(4-methylthiazol-2-yl)methylthio]ethyl}-S-methylisothiourea.
Reference： [1]Patent: US4200578,1980,A
  • 4
  • [ 50398-72-6 ]
  • [ 951122-37-5 ]
  • 2,6-difluoro-3-[(4-methyl-1,3-thiazol-2-yl)methoxy]benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 12h; A 25-mL round bottom flask equipped with a magnetic stirrer was charged with chloro compound 46a (160 mg, 1.1 mmol), DMF (2.0 mL), K2CO3 (400 mg, 3.0 mmol), and <strong>[951122-37-5]2,6-difluoro-3-hydroxybenzamide</strong> (250 mg, 1.5 mmol). The reaction mixture was stirred at room temperature for 12 hours then water was added. The solid was collected by filtration and washed with water. After air drying, the solid was triturated with CH2Cl2. There was obtained the desired product (202 mg, 65% yield) as white solid. 1H NMR (CDCl3, 300 MHz) delta: 7.18-7.1 1 (m, 1H), 6.97 (s, 1H), 6.94-6.87 (m, 1H), 5.4 (s, 2H), 2.44 (s, 3H).
Reference： [1]Patent: WO2013/142712,2013,A1 .Location in patent: Page/Page column 68; 69

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