Sodium p-toluenesulfinate → Methyl 4-(4-{[(4-Methylphenyl)sulfonyl]methyl}-1,3-thiazol-2-yl)benzoate

HRID 1526839Notes

Reaction equation

HRID 1526839 reaction equation
Cl[CH2:2][C:3]1[N:4]=[C:5]([C:8]2[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][CH:9]=2)[S:6][CH:7]=1.[CH3:18][C:19]1[CH:24]=[CH:23][C:22]([S:25]([O-:27])=[O:26])=[CH:21][CH:20]=1.[Na+]>CN(C=O)C>[CH3:18][C:19]1[CH:24]=[CH:23][C:22]([S:25]([CH2:2][C:3]2[N:4]=[C:5]([C:8]3[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][CH:9]=3)[S:6][CH:7]=2)(=[O:27])=[O:26])=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 2723791Sodium p-toluenesulfinateHCID 45156786Methyl 4-[4-(chloromethyl)-1,3-thiazol-2-yl]benzoate

Product 1

HCID 68278235Methyl 4-(4-{[(4-Methylphenyl)sulfonyl]methyl}-1,3-thiazol-2-yl)benzoateYield 77%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Method A. Reaction of chloride 51 (402 mg, 1.5 mmol) and sodium 4-methylbenzenesulfinate (294 mg, 1.7 mmol) in dry DMF (10 mL) gave benzoate 52 (446 mg, 77%) as a white powder: mp (EtOAc) 160-161° C.; 1H NMR (CDCl3) δ 8.05 (ddd, J=8.6, 1.9, 1.7Hz, 2.H, H-2, H-6), 7.77 (ddd, J=8.6, 1.9, 1.7Hz, 2 H, H-3, H-5), 7.64 (ddd, J=8.3, 1.9, 1.7Hz, 2 H, H-2″, H-6″), 7.42 (s, 1 H, H-5′), 7.27 (br d, J=8.3Hz, 2 H, H-3″, H-5″), 4.60 (s, 2 H, CH2SO2), 3.94 (s, 3 H, OCH3), 2.41 (s, 3H, CH3); MS m/z 388.6 (MH+, 100%). Anal. calcd for C19H17NO4S2: C, 58.90; H, 4.42; N, 3.61. Found: C, 58.83; H, 4.33; N, 3.55%.

Sources & evidence

ORD record
ord-ee16091ffae44e838ddb9ec99a6105ba
Source dataset
uspto-grants-2015_07
Patent number
US09085570B2

Reaction notes

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