Hydrochloric Acid → HCID 78321980, compound

HRID 1051291Notes

Reaction equation

HRID 1051291 reaction equation
[N:1]1([C:6]2[CH:7]=[C:8]([C:19]3[S:20][C:21]([C:25]([O-:27])=[O:26])=[C:22]([CH3:24])[N:23]=3)[CH:9]=[CH:10][C:11]=2[O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.O1CCCC1.CO.[OH-].[Na+].Cl>O>[N:1]1([C:6]2[CH:7]=[C:8]([C:19]3[S:20][C:21]([C:25]([OH:27])=[O:26])=[C:22]([CH3:24])[N:23]=3)[CH:9]=[CH:10][C:11]=2[O:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21899815MeOH tetrahydrofuranHCID 131736096HCID 131736096, compound

Product 1

HCID 78321980HCID 78321980, compoundYield 44.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A reaction mixture solution was prepared by dissolving 20.2 mg of 2-[3-(1H-imidazol-1-yl)-4-phenoxyphenyl]-4-methyl-1,3-thiazole-5-carboxylate obtained above in 1 mL of a mixed solution of tetrahydrofuran/methanol=1/1 and adding 0.2 mL of 2 M sodium hydroxide aqueous solution. The reaction mixture was stirred at 50° C. for 2 hours. After the addition of 0.2 mL of 2 M hydrochloric acid to the reaction mixture solution under stirring, 3 mL of water was added and extraction was performed using 4 mL of ethyl acetate. The organic phase was concentrated, followed by purifying using a conventional method to obtain 9.0 mg of 2-[3-(1H-imidazol-1-yl)-4-phenoxyphenyl]-4-methyl-1,3-thiazole-5-carboxylic acid.

Workup

  1. customA reaction mixture solution was prepared
  2. stirringunder stirring
  3. extractionextraction
  4. concentrationThe organic phase was concentrated
  5. customby purifying

Sources & evidence

ORD record
ord-3870aefc5a5e4fbba4788048c5d7367f
Source dataset
uspto-grants-2016_07
Patent number
US09388174B2

Reaction notes

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