Clonidine → HCID 12783890, compound

HRID 2166821Notes

Reaction equation

HRID 2166821 reaction equation
[CH3:1][C:2]1[S:3][C:4]([C:7]([OH:9])=O)=[CH:5][N:6]=1.[Cl:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[C:12]=1[NH:18][C:19]1[NH:20][CH2:21][CH2:22][N:23]=1>O1CCCC1.CS(C)=O>[CH3:1][C:2]1[S:3][C:4]([C:7]([N:23]2[CH2:22][CH2:21][N:20]=[C:19]2[NH:18][C:12]2[C:13]([Cl:17])=[CH:14][CH:15]=[CH:16][C:11]=2[Cl:10])=[O:9])=[CH:5][N:6]=1

Participants

5

Reactant 2

HCID 2803ClonidineHCID 988455-Thiazolecarboxylic acid, 2-methyl-

Product 1

HCID 12783890HCID 12783890, compoundYield 72.6%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

3.15 g (22.0 millimoles) of 2-methyl-thiazole-5-carboxylic acid are dissolved in 500 ml of absolute tetrahydrofuran and 50 ml of absolute dimethylsulfoxide, 3.6 g (22.2 millimoles) of N,N'-carbonyldiimidazole are added and the mixture is stirred for 45 minutes at room temperature. A solution of 5.0 g (21.7 millimoles) of 2-(2',6'-dichlorophenylamino)-2-imidazoline in 100 ml of absolute tetrahydrofuran is then added dropwise and the mixture is stirred overnight at room temperature. The solvents are stripped off under reduced pressure on a rotary evaporator and the residue is stirred thoroughly with 100 ml of 0.5 percent strength sodium bicarbonate solution, whereupon crystallization occurs. The crystals are filtered off, washed with water and dried under reduced pressure, over a phosphorus pentoxide desiccant. 5.6 g of crude 1-(2-methylthiazol-5-oyl)-2-(2',6'-dichlorophenylamino)-2-imidazoline are obtained and are recrystallized from isopropanol, giving 2.7 g of pure product, of melting point 183°-185° C.

Workup

  1. stirringthe mixture is stirred overnight at room temperature
  2. customThe solvents are stripped off under reduced pressure on a rotary evaporator
  3. stirringthe residue is stirred thoroughly with 100 ml of 0.5 percent strength sodium bicarbonate solution, whereupon crystallization
  4. filtrationThe crystals are filtered off
  5. washwashed with water
  6. dry with materialdried under reduced pressure, over a phosphorus pentoxide desiccant

Sources & evidence

ORD record
ord-6d57520cde0b4fc2af15470171753765
Source dataset
uspto-grants-1983_06
Patent number
US04389403

Reaction notes

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