Hydrochloric Acid → HCID 68887523, compound

HRID 1294226Notes

Reaction equation

HRID 1294226 reaction equation
Cl[CH2:2][C:3]1[CH:4]=[C:5]([CH:20]=[CH:21][CH:22]=1)[O:6][CH2:7][C:8]1[N:9]=[C:10]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[O:11][C:12]=1[CH3:13].[SH:23][C:24]1[CH:25]=[C:26]([CH:30]=[CH:31][CH:32]=1)[C:27]([OH:29])=[O:28].CN(C)C=O.Cl>O.C(N(CC)CC)C>[CH3:13][C:12]1[O:11][C:10]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[N:9][C:8]=1[CH2:7][O:6][C:5]1[CH:4]=[C:3]([CH:22]=[CH:21][CH:20]=1)[CH2:2][S:23][C:24]1[CH:25]=[C:26]([CH:30]=[CH:31][CH:32]=1)[C:27]([OH:29])=[O:28]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 95737Benzoic acid, 3-mercapto-HCID 108815514-(3-Chloromethylphenoxymethyl)-5-methyl-2-phenyloxazole

Product 1

HCID 68887523HCID 68887523, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8471TriethylamineSolvent

Procedure

To a mixture of 4-(3-chloromethylphenoxymethyl)-5-methyl-2-phenyloxazole (3.00 g), 3-mercaptobenzoic acid (1.47 g) and N,N-dimethylformamide (30 mL) was dropwise added triethylamine (2.13 g) at room temperature. The reaction mixture was stirred at room temperature for 1 hr. The reaction mixture was poured into water, acidified with 2N hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to give crystals (3.70 g, yield 90%) of 3-[3-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzylthio]benzoic acid from a fraction eluted with acetone-hexane (1:1, v/v). Recrystallization from ethyl acetate gave colorless prism crystals. melting point: 129-130° C.

Workup

  1. customat room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8903d9cbc0194d3eafd0e40d46e0d15b
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

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