Hydrochloric Acid → HCID 86751016, compound

HRID 1421993Notes

Reaction equation

HRID 1421993 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:13]2[S:14][CH:15]=[C:16]([C:18]3[CH:23]=[C:22]([CH2:24][NH:25][CH3:26])[C:21]([O:27]COC)=[C:20]([C:31]([O:33]C)=[O:32])[CH:19]=3)[N:17]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH3:12])[CH3:2].Cl.[OH-].[Na+]>CO>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:13]2[S:14][CH:15]=[C:16]([C:18]3[CH:23]=[C:22]([CH2:24][NH:25][CH3:26])[C:21]([OH:27])=[C:20]([C:31]([OH:33])=[O:32])[CH:19]=3)[N:17]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH3:12])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 14798Sodium HydroxideHCID 18707270HCID 18707270, compound

Product 1

HCID 86751016HCID 86751016, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

In 20 ml of methanol was dissolved 150 mg of 2-(3,4-diethoxyphenyl)-4-(3-methoxycarbonyl-4-methoxymethoxy-5-methylaminomethylphenyl)thiazole. Thereto was added 0.2 ml of 10% hydrochloric acid. The mixture was stirred at 60° C. for 30 minutes. 2 ml of 10% sodium hydroxide was added, and the mixture was refluxed for 1 hour with heating. The reaction mixture was made neutral with 10% hydrochloric acid and the solvent was removed by distillation. The residue was mixed with ethanol. The insoluble was collected by filtration, washed with water, dried and recrystallized from dimethylformamide to obtain 35 mg of 2-(3,4-diethoxyphenyl-4-(3-carboxy-4-hydroxy-5-methylaminomethylphenyl)thiazole.

Workup

  1. temperaturethe mixture was refluxed for 1 hour
  2. temperaturewith heating
  3. customthe solvent was removed by distillation
  4. additionThe residue was mixed with ethanol
  5. filtrationThe insoluble was collected by filtration
  6. washwashed with water
  7. customdried
  8. customrecrystallized from dimethylformamide

Sources & evidence

ORD record
ord-0213fb0e4bcf425bb30e0a49884eada2
Source dataset
uspto-grants-2000_06
Patent number
US06080764

Reaction notes

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