ChemicalBook CAS DataBase List 10-Phenyl-10H-phenothiazine

10-Phenyl-10H-phenothiazine synthesis

12synthesis methods

Product Name:10-Phenyl-10H-phenothiazine
CAS Number:7152-42-3
Molecular formula:C18H13NS
Molecular Weight:275.37

92-84-2

591-50-4

7152-42-3

Phenothiazine (500 mg, 2.50 mmol) was dissolved in anhydrous toluene (5 mL) under nitrogen protection, and iodobenzene (310 mg, 2.2 mmol), sodium tert-butanolate (0.5 mL), and tris(dibenzylideneacetone)dipalladium (Pd2(dba)3, 46 mg, 0.05 mmol) were added in sequence. The reaction mixture was transferred to a sealed tube and the reaction was stirred at 160 °C for 16 hours. After completion of the reaction, it was cooled to room temperature. The organic layer was separated and the aqueous layer was extracted with dichloromethane (2 x 15 mL). The organic phases were combined, dried over anhydrous sodium sulfate (Na2SO4) and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (eluent: petroleum ether/ethyl acetate= 20:1) to afford 10-phenylphenothiazine (600 mg, 87.3%) as a white solid with a melting point of 205 °C. Nuclear magnetic resonance hydrogen spectrum (1H-NMR, 300 MHz, acetone-d6): δ 7.70 (t, J = 7.5 Hz, 2H), 7.57 (t, J = 7.2 Hz, 1H), 7.44 (d, J = 7.8 Hz, 2H), 7.06 (d, J = 7.5 Hz, 2H), 6.92 (t, J = 7.2 Hz, 2H), 6.89 (t , J = 7.2 Hz, 2H), 6.23 (d, J = 8.1 Hz, 2H). Nuclear magnetic resonance carbon spectrum (13C NMR, 100 MHz, acetone-d6): δ 144.98, 141.82, 131.64, 131.37, 129.07, 127.31, 123.37, 120.90, 116.96. The electrospray high-resolution mass spectrometry (ESI-HRMS) m/z calculated value of C18H14NS ([M + H] +) was 276.0841 and the measured value was 276.0842.

108-86-1 Synthesis

108-86-1
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92-84-2
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7152-42-3
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$45.00/250mg

Yield:7152-42-3 97%

Reaction Conditions:

with tris-(dibenzylideneacetone)dipalladium⁽⁰⁾;potassium tert-butylate;tri tert-butylphosphoniumtetrafluoroborate in toluene for 20 h;Inert atmosphere;Reflux;

Steps:

General procedure A - synthesis of N-phenylphenothiazines.
General procedure: N-phenylphenothiazineswere synthesized similarily to the reported procedure [S2]. Phenothiazine(1.00 equiv) was dissolved in anhydrous toluene (0.51 M). Bromobenzene(1.22 equiv), KOt-Bu (1.29 equiv) and (t-Bu)3PHBF4 (6 mol %) were added, followedby Pd2dba3 (3 mol % as 6 mol % Pd). The reaction mixture was degassed usingthree freeze-pump-thaw cycles and finally stirred under reflux for 20 °h. Afterreaching room temperature, 100 mL EtOAc and 50 mL water were added to thereaction mixture. After phase separation, the aqueous phase was extractedadditionally with 3 × 100 mL EtOAc. The combined organic phases were dried overNa2SO4, the solvent evaporated and the crude product purified by columnchromatography.

References:

Speck, Fabienne;Rombach, David;Wagenknecht, Hans-Achim [Beilstein Journal of Organic Chemistry,2019,vol. 15,p. 52 - 59] Location in patent:supporting information

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92-84-2
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$10.00/5g

591-50-4 Synthesis

591-50-4
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$10.00/1g

7152-42-3
67 suppliers
$45.00/250mg

References