2-Methylphenyl isothiocyanate synthesis
- Product Name:2-Methylphenyl isothiocyanate
- CAS Number:614-69-7
- Molecular formula:C8H7NS
- Molecular Weight:149.21
74467-03-1
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Yield:614-69-7 94%
Reaction Conditions:
with OuadraPure Thiaurea resin;SIO2-pyridine in acetonitrile at 50; for 0.166667 h;Flow reactor;
Steps:
1-Isothiocyanato-2-methylbenzene (6b)
General procedure: General flow procedure for the conversion of chloroximes into isothiocyanates: A solution of a chloroxime substrate was prepared in 2 mL MeCN (0.25-0.5 M) and injected into a sample loop mounted on the R2-flow unit. This solution was subsequently pumped at a flow rate of 0.2 mL/min into a heated Omnifit glass column (50 °C, 10 cm length, 6.6 mm i.d.) placed in a glass jacket on the R4-flow unit. This glass column was filled with a mixture of the immobilised base (SiO2-pyridine, 1.2 equiv [or 2.5 equiv in case of entries 13, 14, 15 in Table 2]) and the immobilised thiourea (QP-TU or QS-MTU, 1.2 equiv). After passing this reactor column the reaction mixture was collected, concentrated by evaporation of the solvent and analysed by 1H NMR spectroscopy. If the product purity was below 90% column chromatography was performed as indicated below (10% EtOAc/90% hexanes).
References:
Baumann, Marcus;Baxendale, Ian R. [Beilstein Journal of Organic Chemistry,2013,vol. 9,p. 1613 - 1619] Location in patent:supporting information
45892-06-6
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