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

HRID 931453Notes

Reaction equation

HRID 931453 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH2:11][C:12]2[N:13]=[C:14]([C:17]3[CH:26]=[CH:25][C:20]([C:21]([O:23]C)=[O:22])=[CH:19][CH:18]=3)[S:15][CH:16]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1>Cl>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([CH2:11][C:12]2[N:13]=[C:14]([C:17]3[CH:26]=[CH:25][C:20]([C:21]([OH:23])=[O:22])=[CH:19][CH:18]=3)[S:15][CH:16]=2)(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

3

Reactant 1

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

Product 1

HCID 682781554-(4-{[(4-Methylphenyl)sulfonyl]methyl}-1,3-thiazol-2-yl)benzoic AcidYield 100%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Reaction of benzoate 52 (407 mg, 1.05 mmol) and 6 M HCl (20 mL) gave acid 53 (392 mg, 100%) as a white solid: mp (H2O) 270-272° C.; 1H NMR δ 13.15 (br s, 1H, CO2H), 8.01 (ddd, J=8.6, 1.9, 1.7 Hz, 2H, H-2, H-6), 7.83 (ddd, J=8.6, 1.9, 1.7 Hz, 2H, H-3, H-5), 7.70 (s, 1H, H-5′), 7.65 (br d, J=8.3, 2H, H-2″, H-6″), 7.41 (br d, J=8.3 Hz, 2H, H-3″, H-5″), 4.87 (s, 2H, CH2SO2), 2.39 (s, 3H, CH3); MS m/z 374.6 (MH+, 100%). Anal. calcd for C18H15NO4S2: C, 57.89; H, 4.05; N, 3.75. Found: C, 57.89; H, 4.07; N, 3.63%.

Sources & evidence

ORD record
ord-fd2c0c88b6904658b4051c9dff79626d
Source dataset
uspto-grants-2016_03
Patent number
US09296732B2

Reaction notes

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