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Chemical Structure| 21892-80-8 Chemical Structure| 21892-80-8

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Chemical Structure| 21892-80-8

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Product Details of [ 21892-80-8 ]

CAS No. :21892-80-8
Formula : C8H7NO2
M.W : 149.15
SMILES Code : O=C1OC2=CC=CC=C2N1C
MDL No. :MFCD00748831
Boiling Point : No data available
InChI Key :QRMRRLXXFHXMBC-UHFFFAOYSA-N
Pubchem ID :30846

Safety of [ 21892-80-8 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302
Precautionary Statements:P280-P305+P351+P338

Application In Synthesis of [ 21892-80-8 ]

* 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 [ 21892-80-8 ]

[ 21892-80-8 ] Synthesis Path-Upstream   1~1

  • 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.
 

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