Diethyl Ether → HCID 178464564, compound

HRID 2419786Notes

Reaction equation

HRID 2419786 reaction equation
I.[NH2:2][NH:3][C:4]([NH:13][CH2:14][CH3:15])=[N:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(OCC)C.[OH-].[Na+].[Cl:23][C:24]1[CH:31]=[CH:30][CH:29]=[C:28]([Cl:32])[C:25]=1[CH:26]=O>C(Cl)Cl.CCCCCC>[CH2:6]([NH:5][C:4]([NH:3][N:2]=[CH:26][C:25]1[C:24]([Cl:23])=[CH:31][CH:30]=[CH:29][C:28]=1[Cl:32])=[N:13][CH2:14][CH3:15])[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 67372,6-DichlorobenzaldehydeHCID 14798Sodium HydroxideHCID 20569835HCID 20569835, compound

Product 1

HCID 178464564HCID 178464564, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8058HexaneSolvent

Procedure

A 10.0 g. portion of 1-amino-2-benzyl-3-ethylguanidine hydroiodide in a mixture of 100 ml. each of diethyl ether, n-hexane and methylene chloride is shaken with 10 ml. of 5N NaOH. A 5.46 g. portion of 2,6-dichlorobenzaldehyde is added and the mixture is shaken and then allowed to stand at room temperature overnight. The organic layer is washed with saturated aqueous sodium chloride, passed through hydrous sodium magnesium silicate and concentrated under reduced pressure. The residue is crystallized from diethyl ether-hexane to give the desired product as a bright yellow solid, m.p. 101°-103° C.

Workup

  1. washThe organic layer is washed with saturated aqueous sodium chloride
  2. concentrationconcentrated under reduced pressure
  3. customThe residue is crystallized from diethyl ether-hexane

Sources & evidence

ORD record
ord-ea61ed6977e942b39f9c165fe7310ad6
Source dataset
uspto-grants-1978_08
Patent number
US04107326

Reaction notes

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