HCID 68278129, compound → HCID 53213343, compound

HRID 1526877Notes

Reaction equation

HRID 1526877 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:19]1[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=1>Cl.O>[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:19]1[CH:20]=[CH:21][C:22]([CH3:25])=[CH:23][CH:24]=1

Participants

4

Reactant 1

HCID 68278129HCID 68278129, compound

Product 1

HCID 53213343HCID 53213343, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of methyl 4-(5-methyl-4-(p-tolylthiomethyl)oxazol-2-yl)benzoate (3.1 g, 8.78 mmol, 1.00 equiv) in 6N hydrochloric acid (90 mL) was stirred overnight at 90° C. The reaction mixture was diluted with 150 mL of water and extracted with 3×150 mL of ethyl acetate. The combined organic layers was washed with 3×50 mL of brine, dried over anhydrous sodium sulfate and concentrated under vacuum to give 2.2 g (74%) of 4-(5-methyl-4-(p-tolylthiomethyl)oxazol-2-yl)benzoic acid as a white solid. LC-MS: (ES, m/z): 381 [M+CH3CN+H]+, 340 [M+H]+, 257, 216, 189, 146, 105. H-NMR: 1HNMR (400 MHz, CDCl3, ppm) δ 8.18-8.09 (dd, 4H), 7.30-7.28 (d, 2H), 7.10-7.08 (d, 2H), 3.95 (s, 2H), 2.32 (s, 3H), 2.08 (s, 3H).

Workup

  1. extractionextracted with 3×150 mL of ethyl acetate
  2. washThe combined organic layers was washed with 3×50 mL of brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-d1e83d4961ec4c31837f97bcb6a3f14b
Source dataset
uspto-grants-2015_07
Patent number
US09085570B2

Reaction notes

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