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Chemical Structure| 62522-63-8 Chemical Structure| 62522-63-8

Structure of 62522-63-8

Chemical Structure| 62522-63-8

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Product Details of [ 62522-63-8 ]

CAS No. :62522-63-8
Formula : C8H6ClNO4S
M.W : 247.66
SMILES Code : O=S(C1=CC=C2N(C)C(OC2=C1)=O)(Cl)=O
MDL No. :MFCD03033702
InChI Key :MRSCMVKREGBNOW-UHFFFAOYSA-N
Pubchem ID :2772060

Safety of [ 62522-63-8 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H302-H312-H314-H332
Precautionary Statements:P280-P305+P351+P338-P310
Class:8
UN#:3261
Packing Group:

Application In Synthesis of [ 62522-63-8 ]

* 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.

  • Upstream synthesis route of [ 62522-63-8 ]

[ 62522-63-8 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 21892-80-8 ]
  • [ 62522-63-8 ]
YieldReaction ConditionsOperation in experiment
91% at 0℃; Inert atmosphere; Schlenk technique; Reflux 3-Methylbenzoxalinone (2) (0.600 g, 4.02 mmol) was added to chlorosulfonic acid (2.343 g,20.1 mmol) in small portions at 0 oC. Then, the reaction mixture was heated to 60 oC for 2 h withstirring. The reaction mixture was cooled to room temperature, and slowly poured into crushed ice toform precipitate. The resulting precipitate was collected by filtration. The solid was dissolved in EtOAcand the organic layer was washed with water, brine, dried over MgSO4, and concentrated in vacuo toafford 3 as a light brown solid (0.903 g, 91percent): 1H NMR (300 MHz, CDCl3) δ 7.99 (dd, J = 8.4, 1.8 Hz,1H), 7.89 (d, J = 1.6 Hz, 1H), 7.17 (d, J = 8.4 Hz, 1H), 3.52 (s, 3H). The data were consistent withliterature values.
46% at 0 - 20℃; for 3 h; 3-Methylbenzo[d]oxazol-2(3H)-one (4.16 mmol) was added in several batches to sulfurochloridic acid (17.5 g) at 0 °C. The resulting solution was allowed to warm to rt and was maintained for 3 h. The reaction mixture was slowly poured into cold (0 °C) brine (200 mL) and the resulting solution was extracted with ethyl acetate (3 x 40 mL). The combined organic layers were dried (sodium sulfate), filtered and concentrated to afford 3-methyl-2-oxo-2,3-dihydrobenzo[d]oxazole-6-sulfonyl chloride in 46percent yield as a light brown solid. 1H NMR (CDCl3) δ 8.00 (d, 1H), 7.97 (s, 1H), 7.16 (d, 1H), 3.52 (s, 3H).
46% at 0 - 20℃; 2. Synthesis of 3-methyl-2-oxo-2,3-dihydrobenzo[d]oxazole-6-sulfonly chloride; 3-Methylbenzo[d]oxazol-2(3H)-one (4.16 mmol) was added in several batches to sulfurochloridic acid (17.5 g) at 0° C. The resulting solution was allowed to warm to rt and was maintained for 3 h. The reaction mixture was slowly poured into cold (0° C.) brine (200 mL) and the resulting solution was extracted with ethyl acetate (3.x.40 mL). The combined organic layers were dried (sodium sulfate), filtered and concentrated to afford 3-methyl-2-oxo-2,3-dihydrobenzo[d]oxazole-6-sulfonyl chloride in 46percent yield as a light brown solid. Data: 1H NMR (CDCl3) δ 8.00 (d, 1H), 7.97 (s, 1H), 7.16 (d, 1H), 3.52 (s, 3H).
46% at 0 - 20℃; 2. Synthesis of 3-methyl-2-oxo-2,3-dihvdrobenzo['d']oxazole-6-sulfonyl chloride.3-Methylbenzo[d]oxazol-2(3H)-one (4.16 mmol) was added in several batches to sulfurochloridic acid (17.5 g) at 0 0C. The resulting solution was allowed to warm to rt and was maintained for 3 h. The reaction mixture was slowly poured into cold (0 0C) brine (200 mL) and the resulting solution was extracted with ethyl acetate (3 x 40 mL). The combined organic layers were dried (sodium sulfate), filtered and concentrated to afford 3-methyl-2-oxo-2,3- dihydrobenzo[d]oxazole-6-sulfonyl chloride in 46percent yield as a light brown solid. 1H NMR (CDCl3) δ 8.00 (d, IH), 7.97 (s, IH), 7.16 (d, IH), 3.52 (s, 3H).
46% With chlorosulfonic acid In chlorosulfonic acid at 0 - 20℃; 3-Methylbenzo[d]oxazol-2(3H)-one (4.16 mmol) was added in several batches to sulfurochloridic acid (17.5 g) at 0° C. The resulting solution was allowed to warm to rt and was maintained for 3 h. The reaction mixture was slowly poured into cold (0° C.) brine (200 mL) and the resulting solution was extracted with ethyl acetate (3.x.40 mL). The combined organic layers were dried (sodium sulfate), filtered and concentrated to afford 3-methyl-2-oxo-2,3-dihydrobenzo[d]oxazole-6-sulfonyl chloride in 46percent yield as a light brown solid. 1H NMR (CDCl3) δ 8.00 (d, 1H), 7.97 (s, 1H), 7.16 (d, 1H), 3.52 (s, 3H).
46% at 0 - 20℃; 2. Synthesis of 3-methyl-2-oxo-2,3-dihvdrobenzo[d"|oxazole-6-sulfonyl chloride.3-Methylbenzo[d]oxazol-2(3H)-one (4.16 mmol) was added in several batches to sulfurochloridic acid (17.5 g) at 0 0C. The resulting solution was allowed to warm to rt and was maintained for 3 h. The reaction mixture was slowly poured into cold (0 0C) brine (200 mL) and the resulting solution was extracted with ethyl acetate (3 x 40 mL). The combined organic layers were dried (sodium sulfate), filtered and concentrated to afford 3-methyl-2-oxo-2,3- dihydrobenzo[d]oxazole-6-sulfonyl chloride in 46percent yield as a light brown solid. 1H NMR (CDCl3) δ 8.00 (d, IH), 7.97 (s, IH), 7.16 (d, IH), 3.52 (s, 3H). Intermediate 34: Synthesis of l-methylindoline-6-sulfonyl chloride.
46% at 0 - 20℃; 3-Methylbenzo[d]oxazol-2(3H)-one (4.16 mmol) was added in several batches to sulfurochloridic acid (17.5 g) at 0° C.
The resulting solution was allowed to warm to rt and was maintained for 3 h.
The reaction mixture was slowly poured into cold (0° C.) brine (200 mL) and the resulting solution was extracted with ethyl acetate (3*40 mL).
The combined organic layers were dried (sodium sulfate), filtered and concentrated to afford 3-methyl-2-oxo-2,3-dihydrobenzo[d]oxazole-6-sulfonyl chloride in 46percent yield as a light brown solid. Data: 1H NMR (CDCl3) δ 8.00 (d, 1H), 7.97 (s, 1H), 7.16 (d, 1H), 3.52 (s, 3H).
46% at 0 - 20℃; for 3 h; 3-methylbenzo[d]oxazol-2(3H)-one (620 mg, 4.16 mmol) was added, in several batches, to chilled sulfurochloridic acid (17.5 g, 150.86 mmol) at 0 °C. The resulting solution was stirred at room temperature for 3 hours, then quenched by adding it slowly to 200 mL of ice/salt. The resulting solution was extracted with ethyl acetate (3 x 40 mL). The organic layers were combined, dried (Na2SO4), filtered and concentrated to afford 0.5 g (46percent) of 3-methyl-2-oxo-2,3- dihydrobenzo[d]oxazole-6-sulfonyl chloride as a light brown solid. 1H NMR (CDCl3) δ 8.00 (d, IH), 7.97 (s, IH), 7.16 (d, IH), 3.52 (s, 3H).

References: [1] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 20, p. 4875 - 4889.
[2] Chemistry of Heterocyclic Compounds, 2011, vol. 47, # 1, p. 90 - 95.
[3] Patent: WO2009/23844, 2009, A2, . Location in patent: Page/Page column 123-124.
[4] Patent: US2010/16297, 2010, A1, . Location in patent: Page/Page column 22.
[5] Patent: WO2010/21797, 2010, A1, . Location in patent: Page/Page column 88.
[6] Patent: US2010/29629, 2010, A1, . Location in patent: Page/Page column 59.
[7] Patent: WO2010/24980, 2010, A1, . Location in patent: Page/Page column 106.
[8] Patent: US2010/22581, 2010, A1, . Location in patent: Page/Page column 32-33.
[9] Patent: WO2007/98418, 2007, A1, . Location in patent: Page/Page column 121; 122.
[10] Pharmaceutical Chemistry Journal, 1976, vol. 10, # 7, p. 868 - 872[11] Khimiko-Farmatsevticheskii Zhurnal, 1976, vol. 10, # 7, p. 23 - 28.
[12] Patent: CN107098846, 2017, A, . Location in patent: Paragraph 2433; 2437; 2438.
  • 2
  • [ 59-49-4 ]
  • [ 62522-63-8 ]
References: [1] Chemistry of Heterocyclic Compounds, 2011, vol. 47, # 1, p. 90 - 95.
[2] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 20, p. 4875 - 4889.
[3] Patent: CN107098846, 2017, A, .
  • 3
  • [ 1216666-32-8 ]
  • [ 62522-63-8 ]
References: [1] Chemistry of Heterocyclic Compounds, 2011, vol. 47, # 1, p. 90 - 95.
 

Historical Records

Technical Information

• Acyl Group Substitution • Alkyl Halide Occurrence • Baeyer-Villiger Oxidation • Barbier Coupling Reaction • Baylis-Hillman Reaction • Benzylic Oxidation • Birch Reduction • Blanc Chloromethylation • Bucherer-Bergs Reaction • Chan-Lam Coupling Reaction • Clemmensen Reduction • Complex Metal Hydride Reductions • Corey-Bakshi-Shibata (CBS) Reduction • Corey-Chaykovsky Reaction • Fischer Indole Synthesis • Friedel-Crafts Reaction • General Reactivity • Grignard Reaction • Henry Nitroaldol Reaction • Hiyama Cross-Coupling Reaction • Horner-Wadsworth-Emmons Reaction • Hydride Reductions • Hydrogenolysis of Benzyl Ether • Kinetics of Alkyl Halides • Kumada Cross-Coupling Reaction • Lawesson's Reagent • Leuckart-Wallach Reaction • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Passerini Reaction • Paternò-Büchi Reaction • Petasis Reaction • Peterson Olefination • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Aldehydes and Ketones • Preparation of Alkylbenzene • Preparation of Amines • Prins Reaction • Reactions of Aldehydes and Ketones • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reformatsky Reaction • Robinson Annulation • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Specialized Acylation Reagents-Carbodiimides and Related Reagents • Specialized Acylation Reagents-Ketenes • Stille Coupling • Stobbe Condensation • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling • Tebbe Olefination • Ugi Reaction • Vilsmeier-Haack Reaction • Wittig Reaction • Wolff-Kishner Reduction

Categories

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[ 62522-63-8 ]

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Related Parent Nucleus of
[ 62522-63-8 ]

Benzoxazoles

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