Nitrogen mustard hydrochloride → 2-(4-Methylpiperazin-1-yl)-1,3-thiazole-5-carbaldehyde

HRID 336834

Reaction equation

HRID 336834 reaction equation
[NH2:1][C:2]1[S:3][C:4]([CH:7]=[O:8])=[CH:5][N:6]=1.C([O-])([O-])=O.[K+].[K+].Cl.Cl[CH2:17][CH2:18][N:19]([CH2:21][CH2:22]Cl)[CH3:20]>CN(C=O)C>[CH3:20][N:19]1[CH2:21][CH2:22][N:1]([C:2]2[S:3][C:4]([CH:7]=[O:8])=[CH:5][N:6]=2)[CH2:17][CH2:18]1

Participants

5

Reactant 3

HCID 5935Nitrogen mustard hydrochlorideHCID 11430Potassium CarbonateHCID 27377982-Amino-1,3-thiazole-5-carbaldehyde

Product 1

HCID 14902342-(4-Methylpiperazin-1-yl)-1,3-thiazole-5-carbaldehydeYield 50.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

In a 25 ml flask are added 0.5 g of 2-aminothiazole-5-carboxaldehyde, 1.35 g of K2CO3 in 5 ml of DMF. After dissolution, 0.901 g of 2-chloro-N-(2-chloroethyl)-N-methylethanamine hydrochloride are added. The mixture is left at room temperature for 1 h then heated to 90° C. for 5 h. Next, the mixture is evaporated, dissolved in 100 ml of water, and the aqueous phase is extracted three times with ethyl acetate. The organic phases are combined, washed with sodium chloride saturated solution, dried over sodium sulfate, filtered, and evaporated to yield 420 mg (50%) of 2-(4-methylpiperazin-1-yl)thiazole-5-carboxaldehyde.

Workup

  1. additionare added
  2. customNext, the mixture is evaporated
  3. dissolutiondissolved in 100 ml of water
  4. extractionthe aqueous phase is extracted three times with ethyl acetate
  5. washwashed with sodium chloride saturated solution
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-39af4352341447feae9be1a7f75ba4c3
Source dataset
uspto-grants-2014_11
Patent number
US08889711B2

Linked notes

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