Potassium Hydroxide → 1-(4-(3-Aminophenyl)thiazol-2-yl)guanidine

HRID 464696Notes

Reaction equation

HRID 464696 reaction equation
Br.[NH:2]([C:6]1[S:7][CH:8]=[C:9]([C:11]2[CH:12]=[C:13]([NH:17]C(=O)OCC)[CH:14]=[CH:15][CH:16]=2)[N:10]=1)[C:3]([NH2:5])=[NH:4].[OH-].[K+]>C(O)C>[NH:2]([C:6]1[S:7][CH:8]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([NH2:17])[CH:12]=2)[N:10]=1)[C:3]([NH2:5])=[NH:4]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 178419570HCID 178419570, compound

Product 1

HCID 1785126111-(4-(3-Aminophenyl)thiazol-2-yl)guanidineYield 70.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 47.1 gm of ethyl N-[3-(2-guanidino-4-thiazolyl)-phenyl]-carbamate hydrobromide, 210 ml of ethanol and 210 ml of a 50% potassium hydroxide solution was refluxed for 15 minutes. After cooling, the white precipitate which had formed was filtered off, dissolved in water and carefully acidified with hydrochloric acid. The resulting solution was made alkaline with an excess of sodium hydroxide solution, and the precipitate formed thereby was filtered off, washed with water and dried, yielding 20 gm of the title compound, m.p. 222°-224° C.

Workup

  1. temperaturewas refluxed for 15 minutes
  2. temperatureAfter cooling
  3. customthe white precipitate which had formed
  4. filtrationwas filtered off
  5. dissolutiondissolved in water
  6. customthe precipitate formed
  7. filtrationthereby was filtered off
  8. washwashed with water
  9. customdried

Sources & evidence

ORD record
ord-ad267791e4654af3bd0a1e4072949b9f
Source dataset
uspto-grants-1985_10
Patent number
US04548944

Reaction notes

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