Ethylenediamine → Clonidine

HRID 542287

Reaction equation

HRID 542287 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1S(O)(=O)=O.[CH2:13]([NH2:16])[CH2:14][NH2:15].[C:17](#[N:19])C>>[CH:6]1[CH:7]=[C:2]([Cl:1])[C:3]([NH:19][C:17]2[NH:16][CH2:13][CH2:14][N:15]=2)=[C:4]([Cl:8])[CH:5]=1

Participants

4

Reactant 3

HCID 3301EthylenediamineHCID 6342AcetonitrileHCID 40513242,6-dichlorobenzenesulfonic Acid

Product 1

HCID 2803Clonidine

Conditions

Temperature
65 °C

Procedure

2,6-dichlorophenylsulfonic acid (1.0 g, 0.0037 m) was added to ethylenediamine (0.5 g, 0.008 m) in the absence of solvent. The reaction exothermed to 35° C. and was diluted with acetonitrile and heated at 65° C. for 7.25 hr. The reaction was concentrated, treated with sodium hydroxide and extracted with methylene chloride. The organic phase was dried and concentrated to yield 0.5 g of clonidine. The product was identified by spectroscopic methods.

Workup

  1. customexothermed to 35° C.
  2. concentrationThe reaction was concentrated
  3. additiontreated with sodium hydroxide
  4. extractionextracted with methylene chloride
  5. customThe organic phase was dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a6f8964ffc3341fca1c328b0030d7bf8
Source dataset
uspto-grants-1987_04
Patent number
US04656291

Linked notes

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