Water → N1,N3-dimethyl-N1-(thiazol-2-yl)propane-1,3-diamine

HRID 1880643Notes

Reaction equation

HRID 1880643 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][CH2:5][NH:6][CH3:7].Br[C:9]1[S:10][CH:11]=[CH:12][N:13]=1.O>C(Cl)(Cl)Cl>[CH3:1][N:2]([C:9]1[S:10][CH:11]=[CH:12][N:13]=1)[CH2:3][CH2:4][CH2:5][NH:6][CH3:7]

Participants

5

Reactant 3

HCID 962WaterHCID 66978N,N'-Dimethyl-1,3-propanediamineHCID 764302-Bromothiazole

Product 1

HCID 69151207N1,N3-dimethyl-N1-(thiazol-2-yl)propane-1,3-diamineYield 60%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
120 °C

Procedure

2.45 g (24.0 mmol) N,N3-dimethylpropane-1,3-diamine was added to 0.36 ml (4.0 mmol) 2-bromothiazole and heated to 120° C. for 1 h. After cooling to RT, dilution with water and chloroform took place. The phases were separated and the aqueous phase was extracted with chloroform. The combined organic phases were dried over MgSO4, filtered, and concentrated in vacuo. Column chromatography (SiO2, DCE/MeOH/25% aq. NH3-soln 4:4:1) was carried out on the residue, yielding 440 mg (2.4 mmol, 59%) N1,N3-dimethyl-N1-(thiazol-2-yl)propane-1,3-diamine.

Workup

  1. temperatureAfter cooling to RT
  2. customThe phases were separated
  3. extractionthe aqueous phase was extracted with chloroform
  4. dry with materialThe combined organic phases were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a6ee07d53c424b61a6ce95f023a0907e
Source dataset
uspto-grants-2012_11
Patent number
US08318774B2

Reaction notes

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