Hydrochloric Acid → HCID 178512609, compound

HRID 1446985Notes

Reaction equation

HRID 1446985 reaction equation
Cl.[NH:2]([C:6]1[S:7][CH:8]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][N:18]3C(=O)C4=CC=CC=C4C3=O)[CH:12]=2)[N:10]=1)[C:3]([NH2:5])=[NH:4].Cl>O.C(O)C.[OH-].[Na+]>[NH:2]([C:6]1[S:7][CH:8]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][NH2:18])[CH:12]=2)[N:10]=1)[C:3]([NH2:5])=[NH:4]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 178479393HCID 178479393, compound

Product 1

HCID 178512609HCID 178512609, compoundYield 35.9%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 14798Sodium HydroxideSolvent2×

Procedure

A mixture of 2-guanidino-4-(3-phthalimidomethylphenyl)thiazole hydrochloride (0.7 g.) in water (30 ml.) and ethanol (30 ml.) and sufficient aqueous sodium hydroxide to give pH 12 was heated under reflux for 30 minutes. The pH was adjusted to approximately 3 with concentrated hydrochloric acid and the mixture heated under reflux for a further 30 minutes. The pH was then adjusted to 12 with dilute sodium hydroxide solution and the mixture extracted with ethyl acetate (50 ml.). This extract was evaporated to dryness to give 2-guanidino-4-(3-aminomethylphenyl)thiazole (0.15 g.), m.p. 155°-160° C. (decomp.).

Workup

  1. customto give pH 12
  2. temperaturewas heated
  3. temperatureunder reflux for 30 minutes
  4. temperaturethe mixture heated
  5. temperatureunder reflux for a further 30 minutes
  6. extractionthe mixture extracted with ethyl acetate (50 ml.)
  7. customThis extract was evaporated to dryness

Sources & evidence

ORD record
ord-4ba8813c32b5423db5e161f35c1b2957
Source dataset
uspto-grants-1982_02
Patent number
US04315009

Reaction notes

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