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

HRID 931427Notes

Reaction equation

HRID 931427 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH2:11][C:12]2[N:13]=[C:14]([C:18]3[CH:27]=[CH:26][C:21]([C:22]([O:24]C)=[O:23])=[CH:20][CH:19]=3)[O:15][C:16]=2[CH3:17])(=[O:10])=[O:9])=[CH:4][CH:3]=1.Cl>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH2:11][C:12]2[N:13]=[C:14]([C:18]3[CH:19]=[CH:20][C:21]([C:22]([OH:24])=[O:23])=[CH:26][CH:27]=3)[O:15][C:16]=2[CH3:17])(=[O:9])=[O:10])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 68278221Methyl 4-(4-{[(4-Chlorophenyl)sulfonyl]methyl}-5-methyl-1,3-oxazol-2-yl)benzoate

Product 1

HCID 682782794-(4-{[(4-Chlorophenyl)sulfonyl]methyl}-5-methyl-1,3-oxazol-2-yl)benzoic AcidYield 100.2%

Procedure

Reaction of benzoate 19 (217 mg, 0.53 mmol) and 6 M HCl (5 mL) gave acid 20 (208 mg, 100%) as a white solid: mp (H2O) 268-271° C.; 1H NMR [(CD3)2SO] δ 13.18 (br s, 1H, CO2H), 8.04 (dd, J=8.6, 1.8 Hz, 2H, H-2, H-6), 7.90 (br dd, J=8.6, 1.8 Hz, 2H, H-3, H-5), 7.81 (ddd, J=8.7, 2.4, 2.0 Hz, 2H, H-2′, H-6′), 7.70 (ddd, J=8.7, 2.4, 2.0 Hz, 2H, H-3′, H-5′), 4.74 (s, 2H, CH2SO2), 2.21 (s, 3H, CH3); MS m/z 393.2 (MH+, 100%), 393.0 (MH+, 35%). Anal. calcd for C18H14ClNO5S: C, 55.18; H, 3.60; N, 3.57. Found: C, 55.22; H, 3.41; N, 3.47%.

Sources & evidence

ORD record
ord-132d6f4e45b94c7c9e34b5e52c0b9765
Source dataset
uspto-grants-2016_03
Patent number
US09296732B2

Reaction notes

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