Hydrochloric Acid → HCID 178479593, compound

HRID 1262644Notes

Reaction equation

HRID 1262644 reaction equation
[NH2:1][NH2:2].C[O:4][C:5](=O)[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]2[N:13]=[C:14]([NH:17][CH:18]=[N:19][NH2:20])[S:15][CH:16]=2)[CH:7]=1.[ClH:22]>C(O)C>[ClH:22].[NH2:20][N:19]=[CH:18][NH:17][C:14]1[S:15][CH:16]=[C:12]([C:8]2[CH:7]=[C:6]([CH:11]=[CH:10][CH:9]=2)[C:5]([NH:1][NH2:2])=[O:4])[N:13]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 9321HydrazineHCID 178497688HCID 178497688, compound

Product 1

HCID 178479593HCID 178479593, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 10 ml. of 95% hydrazine is added 3-[2-[(aminoiminomethyl)amino]-4-thiazolyl]benzoic acid methyl ester (1.1 g., 0.004 mole). This is stirred for 1 hour at room temperature. The product precipitates out and is filtered off and rinsed with ethanol. The filtrate is reduced to dryness and ethanol is added to the residue, and the insoluble material is filtered off and combined with previously filtered solid to give a crude yield of about 1 g. of the carboxhydrazide. This crude solid is added to 40 ml. ethanol and to this is added 10 ml. of ethanolic HCl solution and the mixture is heated briefly at reflux temperature. The suspension that forms is filtered off and recrystallized from 90% aqueous ethanol to give 0.65 g. of the desired product, m.p. 275° C. (dec.).

Workup

  1. customThe product precipitates out
  2. filtrationis filtered off
  3. washrinsed with ethanol
  4. additionis added to the residue
  5. filtrationthe insoluble material is filtered off
  6. customto give a crude yield of about 1 g
  7. additionThis crude solid is added to 40 ml
  8. temperatureat reflux temperature
  9. filtrationThe suspension that forms is filtered off
  10. customrecrystallized from 90% aqueous ethanol
  11. customto give 0.65 g

Sources & evidence

ORD record
ord-79c76b8d3d1f4e08a4584caba3c58782
Source dataset
uspto-grants-1984_06
Patent number
US04452985

Reaction notes

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