Acetic Acid → HCID 178512115, compound

HRID 262767Notes

Reaction equation

HRID 262767 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([Cl:10])[C:3]=1[CH:4]=O.I.[NH2:12][NH:13][C:14]([NH:16][CH2:17][C:18]1[O:22][CH:21]=[CH:20][CH:19]=1)=[NH:15].C(O)(=O)C.[OH-].[Na+]>CCOCC.C(O)C.O>[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([Cl:10])[C:3]=1[CH:4]=[N:12][NH:13][C:14]([NH:16][CH2:17][C:18]1[O:22][CH:21]=[CH:20][CH:19]=1)=[NH:15]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 67372,6-DichlorobenzaldehydeHCID 14798Sodium HydroxideHCID 178506605HCID 178506605, compound

Product 1

HCID 178512115HCID 178512115, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 1.75 g. of 2,6-dichlorobenzaldehyde and 2.82 g. of 1-amino-3-furfurylguanidine hydriodide in 15 ml. of glacial acetic acid is heated at 100° C. for one hour, cooled, and diluted with absolute ether until crystallization occurs. Filtration gives 3.51 g. of gray-colored crystals. The crystals are dissolved by warming in absolute ethanol and the solution is treated with excess 10N sodium hydroxide and diluted with water to turbidity. Chilling and filtration give 2.00 g. of nearly colorless crystals. Two recrystallizations from aqueous ethanol, using activated charcoal, give the desired product as colorless crystals, m.p. 134°-135.5° C.

Workup

  1. temperaturecooled
  2. filtrationFiltration
  3. customgives 3.51 g
  4. dissolutionThe crystals are dissolved
  5. temperatureChilling
  6. filtrationfiltration
  7. customgive 2.00 g
  8. customTwo recrystallizations from aqueous ethanol

Sources & evidence

ORD record
ord-f2f5f739fc294997b70d42275b177bfb
Source dataset
uspto-grants-1979_05
Patent number
US04154947

Reaction notes

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