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[ CAS No. 26018-73-5 ]

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Chemical Structure| 26018-73-5
Chemical Structure| 26018-73-5
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CAS No. :26018-73-5 MDL No. :MFCD07377059
Formula : C9H5ClO2S Boiling Point : 408.6°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :212.65 g/mol Pubchem ID :7141919
Synonyms :

Safety of [ 26018-73-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 26018-73-5 ]

  • Upstream synthesis route of [ 26018-73-5 ]
  • Downstream synthetic route of [ 26018-73-5 ]

[ 26018-73-5 ] Synthesis Path-Upstream   1~3

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YieldReaction ConditionsOperation in experiment
98%
Stage #1: With lithium hydroxide; water In tetrahydrofuran at 20℃; for 4 h;
Stage #2: With hydrogenchloride In tetrahydrofuran; water
To a solution of 600 mg (3.23 mmol) of 4-chloro-2-nitro-benzaldehyde in DMF (7 ml) were added 559 mg (4.04 mmol) of potassium carbonate and 294 μl (3.23 mmol) of methyl thioglycolate at 0° C. The reaction mixture was stirred for 30 min at 0° C. and then for 24 h at RT. Then the mixture was poured into ice-water and the precipitate was collected by filtration and dissolved in ethyl acetate. The solution was dried (MgSO4) and concentrated to yield 630 mg (86percent) of 6-chloro-benzo[b]thiophene-2-carboxylic acid methyl ester as a white solid. 1HNMR (CDCl3, 300 MHz): δ 3.95 (s, 3H), 7.88 (dd, J=8.6 and 1.9 Hz, 1H), 7.79 (d, J=8.6 Hz, 1H), 7.85 (d, J=1.9 Hz, 1H), 8.02 (s, 1H).To a solution of 630 mg (2.78 mmol) of 6-chloro-benzo[b]thiophene-2-carboxylic acid methyl ester in THF (5 ml) were added 6.95 ml of 1N LiOH-solution and the reaction mixture was stirred at RT for 4 h. The pH was then adjusted to 2-3 by addition of 1N HCl and the mixture was extracted with ethyl acetate. The combined organic extracts were washed with brine, dried (MgSO4) and concentrated to yield 579 mg (98percent) of 6-chloro-benzo[b]thiophene-2-carboxylic acid as white solid. MS (ISP) 211.0 (M-H)-.In analogy to example S3 (steps a to b) 139 mg (0.65 mmol) of 6-chloro-benzo[b]thiophen-2-carboxylic acid were converted into 52 mg (0.14 mmol) of (6-chloro-benzo[b]thiophen-2-ylmethyl)-[2-(3,4-dichloro-phenyl)-ethyl]-amine. The product was obtained as colorless liquid. MS (ISP) 370.0 (M+H)+.
60%
Stage #1: With lithium hydroxide monohydrate; water In tetrahydrofuran at 20℃;
To a solution of compound B-101 (10 g, 44 mmol) in tetrahydrofuran (200 mL) and water ( 10 mL) was added lithium hydroxide monohydrate (5.6 g, 0.13 mol). The reaction mixture was stirred at room temperature overnight. On completion, the reaction mixture was concentrated in vacuo to remove tetrahydrofuran and poured into water (400 mL). The pH was adjusted to 3 with 4M hydrochloric acid, resulting in formation of a solid. The solid was collected by filtration, washed with water and dried in vacuo to give compound B-102 (5.6 g, 60percent yield) as a white solid. LCMS: (ES+) m/z (M+H)+ = 212.9.
Reference: [1] Patent: US2007/185113, 2007, A1, . Location in patent: Page/Page column 13
[2] Patent: WO2016/100184, 2016, A1, . Location in patent: Paragraph 00270
[3] Journal of Medicinal Chemistry, 2007, vol. 50, # 20, p. 4793 - 4807
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YieldReaction ConditionsOperation in experiment
77% at 20℃; for 16 h; To a solution of ethyl 6-chlorobenzothiophene-2-carboxylate Xl-9a (9.00 g, 37.5 mmol) inEtOH was added 3 N NaOH (24.9 ml, 74.7 mmol) and the reaction mixture was stirred at20 room temperature for 16h. Progress of the reaction was monitored by TLC. Aftercompletion, the reaction mixture was concentrated under vacuum. The residue wasdiluted with H20 (200 ml), acidified with 2 N HCI and extracted with EtOAc (2 x 300 ml).The organic layer was separated, dried over anhydrous Na2S04 and concentrated undervacuum to afford 6-chlorobenzothiophene-2-carboxylic acid Xl-9b (6.1 0 g) as an off-whitesolid.This compound was used as such for the next reaction without further purification.Yield: 77percent5 1H NMR (400 MHz, DMSO-d5) o 8.00 (d, J=8.31 Hz, 2H) 8.10 (s, 1 H) 8.21 (s, 1 H) 13.52(brs, 1 H).
Reference: [1] Patent: WO2018/122232, 2018, A1, . Location in patent: Page/Page column 245; 246
[2] Patent: WO2015/42397, 2015, A1, . Location in patent: Paragraph 000923
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Reference: [1] Patent: WO2015/42397, 2015, A1,
[2] Patent: WO2016/100184, 2016, A1,
[3] Patent: WO2018/122232, 2018, A1,
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