ChemicalBook CAS DataBase List 4-Methylbenzyl isocyanate

4-Methylbenzyl isocyanate synthesis

7synthesis methods

Product Name:4-Methylbenzyl isocyanate
CAS Number:56651-57-1
Molecular formula:C9H9NO
Molecular Weight:147.17

530-62-1 Synthesis

530-62-1
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104-84-7
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56651-57-1
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$60.00/100mg

Yield: 100%

Reaction Conditions:

in tetrahydrofuran at 70;Product distribution / selectivity;

Steps:

79
To a solution of 4-methylbenzylamine (1.5 mL, 1 1.8 mmol) in THF (30mL) added CDI (2.1 mol eq, 3.8g) and the mixture was heated at 70°C overnight. The reaction mixture was evaporated, water was added and the aqueous phase was extracted with EtOAc (3x30 mL). The recombined organic phases were anhydrified over Na₂SO₄ and evaporated at reduced pressure to give a white solid (1 1.78 mmol, 2.53g, quantitative yield). The solid obtained (0.83 g, 3.88 mmol) was dissolved in DMF (20 mL) and the bicyclic amine If was added (0.8 mol eq, 0.62g), then the mixture obtained was heated at 100°C overnight. The solvent was removed at reduced pressure and the residue was purified by crystallization from hot MeOH to give the product as pale yellow solid (0.078g, 8%Yield). ¹HNMR (DMSO, 200 MHz) δ 2.27 (s, 3H), 4.24 (d, 2H, J=6), 4.59 (s, 2H), 6.28 (t, 1H), 4.47 (dd, 1H), 6.80 (t, 1H, J=8), 7.1 1-7.21 (m, 4H), 7.77 (dd, 1H, J=2), 8.07 (s, 1H), 10.63 (bs, 1H). [M⁺¹] 31 1.99 (C₁₇H₁₇N₃O₃ requires 31 1.34).

References:

PHARMESTE S.R.L.;NAPOLETANO, Mauro;TREVISANI, Marcello;PAVANI, Maria Giovanna;FRUTTAROLO, Francesca WO2011/120604, 2011, A1 Location in patent:Page/Page column 116; 117

32315-10-9 Synthesis