Hydrochloric Acid → HCID 15480888, compound

HRID 567169Notes

Reaction equation

HRID 567169 reaction equation
[CH3:1]I.[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[NH:11][C:12](=[S:20])[O:13][C:14]=2[CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[CH:6][CH:5]=1.[OH-].[Na+].Cl>O.CN(C)C=O>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]=[C:12]([S:20][CH3:1])[O:13][C:14]=2[CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 15480887HCID 15480887, compound

Product 1

HCID 15480888HCID 15480888, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Methyl iodide (0.34 ml) was dropwise added to a mixture of 3-[4-(4-chlorophenyl)-2-thioxo-4-oxazolin-5-yl]propionic acid (1.42 g), an aqueous solution of 2N sodium hydroxide (5.5 ml) and N,N-dimethylformamide (15 ml), with cooling with ice. After the reaction mixture was stirred for 30 minutes, water was added to the resulting reaction mixture, which was then acidified with 2 N hydrochloric acid. The crystals thus precipitated were collected by filtration to obtain 4-(4-chlorophenyl)-2-methylthio-5-oxazolepropionic acid (1.45 g, 97%). This was recrystallized from ethanol to give colorless needles. mp 183-184° C.

Workup

  1. customThe crystals thus precipitated
  2. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-543800cc422e4e239ad5043204961a16
Source dataset
uspto-grants-2001_01
Patent number
US06177452B1

Reaction notes

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