Hydrochloric Acid → N-Methyl-N-(3,4-dichlorostyryl)acetamidine hydrochloride

HRID 972302Notes

Reaction equation

HRID 972302 reaction equation
[CH3:1][N:2]([CH:6]=[CH:7][C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([Cl:15])[CH:9]=1)[C:3](=[NH:5])[CH3:4].ClC1C=C(C=CC=1Cl)C=CNC(=N)C.FS(OC)(=O)=O.[OH-].[Na+].Cl>CC(C)=O.ClCCl>[ClH:14].[CH3:1][N:2]([CH:6]=[CH:7][C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([Cl:15])[CH:9]=1)[C:3](=[NH:5])[CH3:4]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 9870Methyl fluorosulfateHCID 14798Sodium HydroxideHCID 53645811N-methyl-N-(3,4-dichlorostyryl)acetamidineHCID 178465601HCID 178465601, compound

Product 1

HCID 86735119N-Methyl-N-(3,4-dichlorostyryl)acetamidine hydrochloride

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6344DichloromethaneSolvent

Procedure

An alternate method for the preparation of N-methyl-N-(3,4-dichlorostyryl)acetamidine involves the N-methylation of N-(3,4-dichlorostyryl)acetamidine (9.2 g., 0.04 mole) with methyl fluorosulfonate (5.7 g., 0.05 mole) in 50 ml. of dichloromethane. The reaction mixture is basified with 10% sodium hydroxide and the organic layer separated, dried, and concentrated to provide the free base which is taken up in acetone and acidified with ethanolic hydrogen chloride. The product thus obtained is crystallized from ethanol-isopropyl ether to afford analytically pure N-METHYL-N-(3,4-DICHLOROSTYRYL)ACETAMIDINE HYDROCHLORIDE, m.p. 238°-239° C., (dec.)(corr.).

Workup

  1. customthe organic layer separated
  2. customdried
  3. concentrationconcentrated
  4. customto provide the free base which
  5. customThe product thus obtained
  6. customis crystallized from ethanol-isopropyl ether

Sources & evidence

ORD record
ord-68a6a79f01434b42a1574e03f458f20a
Source dataset
uspto-grants-1977_10
Patent number
US04052455

Reaction notes

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