Hydrochloric Acid → HCID 68886942, compound

HRID 1294353Notes

Reaction equation

HRID 1294353 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:30][C:31]([O:33]C)=[O:32])[CH:5]=[CH:6][C:7]=1[S:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH2:17][C:18]2[N:19]=[C:20]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[O:21][C:22]=2[CH3:23])[CH:11]=1.[OH-].[Na+].O1CCCC1.Cl>O.CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:30][C:31]([OH:33])=[O:32])[CH:5]=[CH:6][C:7]=1[S:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH2:17][C:18]2[N:19]=[C:20]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[O:21][C:22]=2[CH3:23])[CH:11]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 68886240HCID 68886240, compound

Product 1

HCID 68886942HCID 68886942, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of methyl 2-[3-chloro-4-[3-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzylthio]phenyl]acetate. (0.47 g), a 1N aqueous sodium hydroxide solution (3 mL), tetrahydrofuran (5 mL) and methanol (5 mL) was stirred at room temperature for 1 hr. The reaction mixture was poured into water and acidified with 1N hydrochloric acid. The precipitated solid was collected by filtration and dried with air to give crystals (0.43 g, yield 94%) of 2-[3-chloro-4-[3-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzylthio]phenyl]acetic acid. Recrystallization from ethyl acetate-methanol gave colorless prism crystals. melting point: 150-151° C.

Workup

  1. filtrationThe precipitated solid was collected by filtration
  2. customdried with air

Sources & evidence

ORD record
ord-d7f25dc9ad574e7abadf38d776622a5c
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

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