Hydrochloric Acid → HCID 15480887, compound

HRID 567154Notes

Reaction equation

HRID 567154 reaction equation
Cl[C:2]1[O:3][C:4]([CH2:14][CH2:15][C:16]([O:18]C)=[O:17])=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=2)[N:6]=1.NC(N)=[S:22].[OH-].[Na+].Cl>O.C(O)C>[Cl:13][C:10]1[CH:11]=[CH:12][C:7]([C:5]2[NH:6][C:2](=[S:22])[O:3][C:4]=2[CH2:14][CH2:15][C:16]([OH:18])=[O:17])=[CH:8][CH:9]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 2723790ThioureaHCID 10990225Methyl 3-[2-chloro-4-(4-chlorophenyl)-5-oxazolyl]propionate

Product 1

HCID 15480887HCID 15480887, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of methyl 2-chloro-4-(4-chlorophenyl)-5-oxazolepropionate (5.72 g), thiourea (4.57 g) and ethanol (70 ml) was stirred under reflux for 30 minutes. An aqueous solution of 2N sodium hydroxide (40 ml) was added to the reaction mixture, and stirred under reflux for an additional 30 minutes. Water was added to the reaction mixture, which was then neutralized with 6N hydrochloric acid. The crystals thus precipitated were collected by filtration to obtain 3-[4-(4-chlorophenyl)-2-thioxo-4-oxazolin-5-yl]propionic acid (5.41 g, yield: 96%). This was recrystallized from ethanol to give colorless needles. mp 196-197° C.

Workup

  1. temperatureunder reflux for 30 minutes
  2. stirringstirred
  3. temperatureunder reflux for an additional 30 minutes
  4. customThe crystals thus precipitated
  5. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-779540bcd950427b8811f5893ce9ae5b
Source dataset
uspto-grants-2001_01
Patent number
US06177452B1

Reaction notes

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