ChemicalBook CAS DataBase List NAPHTHALENE, 1-CYCLOPROPYL-4-ISOTHIOCYANATO-

NAPHTHALENE, 1-CYCLOPROPYL-4-ISOTHIOCYANATO- synthesis

11synthesis methods

Product Name:NAPHTHALENE, 1-CYCLOPROPYL-4-ISOTHIOCYANATO-
CAS Number:878671-95-5
Molecular formula:C14H11NS
Molecular Weight:225.31

75-15-0
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878671-94-4 Synthesis

878671-94-4
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NAPHTHALENE, 1-CYCLOPROPYL-4-ISOTHIOCYANATO-

878671-95-5
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$174.00/5g

Yield: 94%

Reaction Conditions:

Stage #1:carbon disulfide;1-amino-4-cyclopropylnaphthalene with potassium carbonate in water;N,N-dimethyl-formamide at 15; for 3.5 h;
Stage #2: with 1,3,5-trichloro-2,4,6-triazine in dichloromethane;water;N,N-dimethyl-formamide at 0; for 1 h;
Stage #3: with water;sodium hydroxide in dichloromethane;N,N-dimethyl-formamide for 2 h;

Steps:

2 Example 2. 4 -cyclopropyl-l-isothiocyanate naphthalene
Example 2. 4 -cyclopropyl-l-isothiocyanate naphthalene [067] To a flask added 4-cyclopropyl-l-naphthylamine prepared by example 1 (66 g), K₂C0₃ (100 g), DMF (80 ml) and water (560 mL), the mixture was stirred at room temperature, then CS₂ (44 mL) was drop wise added to the mixture in 5 min. After the addition was complete, the mixture was stirred for another 3.5 hours at room temperature (15°C). Then, the mixture was cooled to 0°C, and a solution of cyanuric chloride (33.6 g) in 250 mL of CH₂C1₂ was drop wise added. After the addition was complete, the mixture was stirred for another 1 hour to complete the conversion. The resulting mixture was added 6 N NaOH (300 mL) and was stirred for another 2 hours. To the resulting mixture added dichloromethane (400 mL) and water (200 mL), then the organic layer was separated and the aqueous layer was extracted with CH₂C1₂ (250 mL><2). The combined organic layers were dried over anhydrous Na₂S0₄, filtered, and the solvent of filtrate was removed via distillation under atmospheric pressure to obtain a brown liquid. The brown liquid was further purified by a short silica gel column (cyclohexane as eluent), then 77.0 g (94%) of colorless liquid 4 -cyclopropyl-l-isothiocyanate naphthalene was obtained. GC-Ms: m/z (EI): 225, 1H MR (400 MHz, CDC1₃): δ 8.43 (m, 1H), 8.12 (m, 1H), 7.62 (m, 2H), 7.33 (d, J=8.0 Hz, 1H), 7.18 (d, J=8.0 Hz, 1H), 2.31 (m, 1H), 1.10 (m, 2H), 0.77 (m, 2H).

References:

SUNSHINE LAKE PHARMA CO., LTD.;CHEN, Weiqiang;LUO, Jian;LIU, Lixue;FAN, Yuping WO2014/198241, 2014, A1 Location in patent:Paragraph 066-067

878671-94-4 Synthesis

878671-94-4
88 suppliers
$45.00/250mg