N,N'-Dimethylurea → HCID 178485109, compound

HRID 544410Notes

Reaction equation

HRID 544410 reaction equation
P(Cl)(Cl)(Cl)=O.[C:6]([NH:10]C)([NH:8][CH3:9])=O.[NH2:12][C:13]1[CH:18]=[C:17]([Cl:19])[C:16]([N:20]=[C:21]2[NH:25][CH2:24][CH2:23][NH:22]2)=[C:15]([Cl:26])[CH:14]=1.O1CCC[CH2:28]1>>[Cl:26][C:15]1[CH:14]=[C:13]([N:12]([CH3:28])[C:6]([NH:8][CH3:9])=[NH:10])[CH:18]=[C:17]([Cl:19])[C:16]=1[N:20]=[C:21]1[NH:25][CH2:24][CH2:23][NH:22]1

Participants

5

Reactant 4

HCID 7293N,N'-DimethylureaHCID 8028Tetrahydrofuran2×HCID 24813Phosphorus oxychlorideHCID 178507681HCID 178507681, compound

Product 1

HCID 178485109HCID 178485109, compound

Procedure

Phosphoryl chloride (4.4 ml, 0.047 M) was added with cooling to dimethylurea (4 g, 0.045 M) in tetrahydrofuran (60 ml). After stirring at room temperature for 5 hours the mixture was added to 2-(4-amino-2,6-dichlorophenylimino) imidazolidine (3.0 g, 0.012 M) in tetrahydrofuran (60 ml). The mixture was refluxed for 18 hours and then evaporated to give an oily solid. The residue was extracted into 2 M HCl, washed with methylene chloride and then basified. Extraction of the alkaline mixture with methyl chloride yielded a gum on evaporation of the extract. The gum was taken up in ethanol and the required guanidino compound (300 mg) crystallised. The product was recrystallised as 2-[2,6-dichloro-4-(1,3-dimethylguanidino)phenylimino]imidazolidine dihydroiodide (MP 320° C.).

Workup

  1. temperatureThe mixture was refluxed for 18 hours
  2. customevaporated
  3. customto give an oily solid
  4. extractionThe residue was extracted into 2 M HCl
  5. washwashed with methylene chloride
  6. extractionExtraction of the alkaline mixture with methyl chloride
  7. customyielded a gum
  8. customon evaporation of the extract
  9. customthe required guanidino compound (300 mg) crystallised
  10. customThe product was recrystallised as 2-[2,6-dichloro-4-(1,3-dimethylguanidino)phenylimino]imidazolidine dihydroiodide (MP 320° C.)

Sources & evidence

ORD record
ord-1996bd2f1fef479da406c1abfca3b17a
Source dataset
uspto-grants-1984_05
Patent number
US04450170

Reaction notes

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