Isobutanol → Clonidine

HRID 2254860Notes

Reaction equation

HRID 2254860 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([Cl:9])[C:3]=1[NH2:4].[NH:10]1[CH2:14][CH2:13][N:12]=[C:11]1S(O)(=O)=O.C(O)C(C)C>C(Cl)(Cl)Cl>[CH:7]1[CH:8]=[C:2]([Cl:1])[C:3]([NH:4][C:11]2[NH:12][CH2:13][CH2:14][N:10]=2)=[C:5]([Cl:9])[CH:6]=1

Participants

5

Reactant 3

HCID 6560IsobutanolHCID 118462,6-DichloroanilineHCID 2745614,5-dihydro-1H-imidazole-2-sulfonic acid

Product 1

HCID 2803ClonidineYield 64%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
125 °C

Procedure

A mixture of 2,6-dichloroaniline (0.162 g, 1 mmol), imidazoline-2-sulfonic acid (0.30 g, 2 mmol) and isobutanol (3 ml) was heated to 125° C. and maintained at this temperature for 16 hours. The mixture was then cooled to room temperature, diluted with CHCl3 (10 ml) and washed twice with 2 ml of aqueous 1 N NaOH. The organic extracts were combined, dried over MgSO4 and concentrated in vacuo to yield a solid which was chromatographed (silica gel, 10:1 CHCl3 /CH3OH saturated with NH3 (g)) to yield 0.147 g (a yield of 64%) of the title compound as a white solid, which was characterized spectroscopically.

Workup

  1. temperaturemaintained at this temperature for 16 hours
  2. temperatureThe mixture was then cooled to room temperature
  3. washwashed twice with 2 ml of aqueous 1 N NaOH
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customto yield a solid which
  7. customwas chromatographed (silica gel, 10:1 CHCl3 /CH3OH saturated with NH3 (g))

Sources & evidence

ORD record
ord-405d26cbe1ab4a88ad1bc978edc384ca
Source dataset
uspto-grants-1993_08
Patent number
US05237072

Reaction notes

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