HCID 178513146, compound → HCID 178478835, compound

HRID 746037Notes

Reaction equation

HRID 746037 reaction equation
[Cl:1][C:2]1[C:13]([N+:14]([O-])=O)=[CH:12][CH:11]=[C:10]([Cl:17])[C:3]=1[CH:4]=[N:5][NH:6][C:7]([NH2:9])=[NH:8]>Cl.C(O)(=O)C>[ClH:1].[ClH:1].[NH2:14][C:13]1[C:2]([Cl:1])=[C:3]([C:10]([Cl:17])=[CH:11][CH:12]=1)[CH:4]=[N:5][NH:6][C:7]([NH2:9])=[NH:8]

Participants

4

Reactant 1

HCID 178513146HCID 178513146, compound

Product 1

HCID 178478835HCID 178478835, compoundYield 182.9%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolvent

Procedure

A hot solution of stannous chloride dihydrate (12.8 g, 56.7 mmol) in concentrated hydrochloric acid (15 cm3) was slowly added to a hot stirred solution of (2,6-dichloro-3-nitrobenzylideneamino)-guanidine (2.0 g, 7.2 mmol) in glacial acetic acid (20 cm3). The solution was cooled and the precipitated white solid collected, dissolved in methanol (30 cm3) and the solution saturated with hydrogen sulphide. After filtering off the inorganic salts the filtrate was concentrated and then diluted with diethyl ether to yield a white solid which was recrystallised from methanol-diethyl ether affording (3-amino-2,6-dichlorobenzylideneamino)-guanidine dihydrochloride (1.4 g) m.p. 218°-220° C. (dec).

Workup

  1. temperatureThe solution was cooled
  2. customthe precipitated white solid collected
  3. dissolutiondissolved in methanol (30 cm3)
  4. filtrationAfter filtering off the inorganic salts the filtrate
  5. concentrationwas concentrated
  6. additiondiluted with diethyl ether
  7. customto yield a white solid which
  8. customwas recrystallised from methanol-diethyl ether

Sources & evidence

ORD record
ord-77543079d4b4400dac56f93fdbe8873c
Source dataset
uspto-grants-1986_07
Patent number
US04602041

Reaction notes

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