Hydrochloric Acid → HCID 10045599, compound

HRID 1392362Notes

Reaction equation

HRID 1392362 reaction equation
C([O:3][C:4]([C:6]1[S:7][C:8]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=2)=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=2[Cl:18])[N:10]=1)=[O:5])C.[OH-].[K+].Cl>CO.O>[Cl:25][C:22]1[CH:21]=[CH:20][C:19]([C:8]2[S:7][C:6]([C:4]([OH:5])=[O:3])=[N:10][C:9]=2[C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=2[Cl:18])=[CH:24][CH:23]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 10001752HCID 10001752, compound

Product 1

HCID 10045599HCID 10045599, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

40 Part A; Ethyl-5-(4-chlorophenyl)-4-(2,4-dichlorophenyl)thiazole-2-carboxylate (4.10 gram, 9.93 mmol) is suspended in methanol (75 mL). A solution of KOH (1.98 gram, 30 mmol) in water (75 mL) is added and the resulting mixture is heated at reflux temperature for 2 hours. The resulting yellow solution is allowed to attain room temperature, poured into water and acidified with 1N aqueous HCl to give a white precipitate. This precipitate is collected by filtration and twice washed with water. Drying in vacuo gives 5-(4-chlorophenyl)-4-(2,4-dichlorophenyl)thiazole-2-carboxylic acid as a white solid (2.59 gram, 68% yield). 1H-NMR (200 MHz, DMSO-d6): δ 9.25 (s, 1H), 7.65-7.72 (m, 1H), 7.28-7.52 (m, 6H).

Workup

  1. temperaturethe resulting mixture is heated
  2. temperatureat reflux temperature for 2 hours
  3. customto attain room temperature
  4. customto give a white precipitate
  5. filtrationThis precipitate is collected by filtration
  6. washtwice washed with water
  7. customDrying in vacuo

Sources & evidence

ORD record
ord-fba37357ba8f4c85b11d63525d5b65fb
Source dataset
uspto-grants-2008_03
Patent number
US07342032B2

Reaction notes

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