methyl 3-(chlorosulfonyl)-4-methylbenzoate synthesis

4synthesis methods

Product Name:methyl 3-(chlorosulfonyl)-4-methylbenzoate
CAS Number:372198-41-9
Molecular formula:C9H9ClO4S
Molecular Weight:248.68

67-56-1 Synthesis

67-56-1
739 suppliers
$9.00/25ml

2548-29-0 Synthesis

2548-29-0
73 suppliers
$24.00/1g

methyl 3-(chlorosulfonyl)-4-methylbenzoate

372198-41-9
25 suppliers
$170.00/500mg

Yield:372198-41-9 60%

Reaction Conditions:

Stage #1: 3-(chlorosulfonyl)-4-methylbenzoic acidwith thionyl chloride for 1 h;Reflux;
Stage #2: methanol for 1 h;

Steps:

4.1.3.9. Methyl 3-(2-((5-cyanopyrazolo[1,5-a]pyridin-3-yl)methylene)-1-methylhydrazinylsulfonyl)-4-methylbenzoate (6i)

3-(Chlorosulfonyl)-4-methylbenzoic acid (200 mg, 0.85 mmol) was refluxed in SOCl₂ (1.0 mL) for 1 h. The solvent was removed in vacuo, then MeOH (5 mL) added and the solution stirred for 1 h. The solvent was removed in vacuo to leave methyl 3-(chlorosulfonyl)-4-methylbenzoate as a pale brown solid (127 mg, 60%). ¹H NMR δ (400 MHz, CDCl₃) 8.72 (d, J = 1.7 Hz, 1H), 8.25 (dd, J = 7.9, 1.7 Hz, 1H), 7.52 (d, J = 7.9 Hz, 1H), 3.97 (s, 3H), 2.86 (s, 3H). LC-MS (APCI^-) 229 (M-Cl+O, 100%). Reaction of 2 (30 mg, 0.18 mmol) and the above sulfonyl chloride (87 mg, 0.35 mmol) using NaHCO₃, after chromatography (eluting with hexanes:EtOAc 2:1 to 1:1 to EtOAc) gave 6i as a yellow solid (53 mg, 74%).

References:

Kendall, Jackie D.;Giddens, Anna C.;Tsang, Kit Yee;Frédérick, Rapha?l;Marshall, Elaine S.;Singh, Ripudaman;Lill, Claire L.;Lee, Woo-Jeong;Kolekar, Sharada;Chao, Mindy;Malik, Alisha;Yu, Shuqiao;Chaussade, Claire;Buchanan, Christina;Rewcastle, Gordon W.;Baguley, Bruce C.;Flanagan, Jack U.;Jamieson, Stephen M.F.;Denny, William A.;Shepherd, Peter R. [Bioorganic and Medicinal Chemistry,2012,vol. 20,# 1,p. 58 - 68] Location in patent:experimental part

99-75-2 Synthesis