Sulfuric Acid → 5-(3,4-dichlorophenyl)-2,3,5,6-tetrahydro-1H-imidazo[1,2-a]imidazole hydrochloride

HRID 1658256Notes

Reaction equation

HRID 1658256 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][C:16]=1[Cl:17])[CH:5](O)[CH2:6][NH:7][C:8]1[NH:9][CH2:10][CH2:11][N:12]=1.S(=O)(=O)(O)O.[OH-].[Na+]>>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]2[N:12]3[CH2:11][CH2:10][NH:9][C:8]3=[N:7][CH2:6]2)[CH:14]=[CH:15][C:16]=1[Cl:17]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 540921273,4-Dichloro-alpha-(2-imidazolin-2-ylaminomethyl)benzyl alcohol

Product 1

HCID 215290445-(3,4-dichlorophenyl)-2,3,5,6-tetrahydro-1H-imidazo[1,2-a]imidazole hydrochloride

Procedure

4.3 parts of 3,4-dichloro-α-(2-imidazolin-2-ylaminomethyl)benzyl alcohol are added portionwise to 16.2 parts of sulfuric acid solution 80% while stirring and cooling. Upon completion, the mixture is stirred for 2 hr. 30 min. at room temperature. The reaction mixture is poured onto ice-water, alkalized with concentrated sodium hydroxide solution and the product in base form is extracted with methylene chloride. The organic layer is dried, filtered and evaporated. The residue is converted into the hydrochloride salt in 2-propanol, yielding 5-(3,4-dichlorophenyl)-2,3,5,6-tetrahydro-1H-imidazo[1,2-a]imidazole hydrochloride; m.p. 298.4°C (dec.).

Workup

  1. temperaturecooling
  2. stirringUpon completion, the mixture is stirred for 2 hr
  3. custom30 min.
  4. customat room temperature
  5. additionThe reaction mixture is poured onto ice-water
  6. extractionthe product in base form is extracted with methylene chloride
  7. customThe organic layer is dried
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-ecced284432843a59edf1606cee6fd01
Source dataset
uspto-grants-1976_06
Patent number
US03963718

Reaction notes

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