Methyl 4-(5-Methyl-4-{[(4-methylphenyl)sulfonyl]methyl}-1,3-oxazol-2-yl)benzoate → 4-(5-Methyl-4-{[(4-methylphenyl)sulfonyl]methyl}-1,3-oxazol-2-yl)benzoic Acid

HRID 931413Notes

Reaction equation

HRID 931413 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:16]=[CH:15][C:10]([C:11]([O:13]C)=[O:12])=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:17][S:18]([C:21]1[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=1)(=[O:20])=[O:19]>Cl>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][C:10]([C:11]([OH:13])=[O:12])=[CH:15][CH:16]=2)=[N:4][C:3]=1[CH2:17][S:18]([C:21]1[CH:22]=[CH:23][C:24]([CH3:27])=[CH:25][CH:26]=1)(=[O:19])=[O:20]

Participants

3

Reactant 1

HCID 68278073Methyl 4-(5-Methyl-4-{[(4-methylphenyl)sulfonyl]methyl}-1,3-oxazol-2-yl)benzoate

Product 1

HCID 532133574-(5-Methyl-4-{[(4-methylphenyl)sulfonyl]methyl}-1,3-oxazol-2-yl)benzoic AcidYield 97%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Reaction of benzoate 3 (1.96 g, 5.1 mmol) and 6 M HCl (50 mL) gave acid 4 (1.83 g, 97%) as a white solid: mp (H2O) 242-245° C.; 1H NMR δ 13.16 (br s, 1H, CO2H), 8.05 (ddd, J=8.6, 1.9, 1.5 Hz, 2H, H-2, H-6), 7.92 (ddd, J=8.6, 1.9, 1.5 Hz, 2H, H-3, H-5), 7.67 (br d, J=8.3 Hz, 2H, H-2′, H-6′), 7.42 (br d, J=8.3 Hz, 2H, H-3′, H-5′), 4.63 (s, 2H, CH2SO2), 2.40 (s, 3H, CH3), 2.13 (s, 3H, CH3); MS m/z 372.8 (MH+, 100%). Anal. calcd for C19H17NO5S: C, 61.44; H, 4.61; N, 3.77. Found: C, 61.67; H, 4.57; N, 3.79%.

Sources & evidence

ORD record
ord-37b74a6a2e1c4275ae2e9d9baf40b33e
Source dataset
uspto-grants-2016_03
Patent number
US09296732B2

Reaction notes

Loading…