3-Chloropropyl(diethyl)amine → HCID 13135892, compound

HRID 2164537Notes

Reaction equation

HRID 2164537 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([NH2:13])=[C:11]([C:14]([O:16][CH3:17])=[O:15])[N:10]=[N:9]2)=[CH:4][CH:3]=1.Cl[CH2:19][CH2:20][CH2:21][N:22]([CH2:25][CH3:26])[CH2:23][CH3:24]>CN(C)C=O>[ClH:1].[CH2:23]([N:22]([CH2:25][CH3:26])[CH2:21][CH2:20][CH2:19][N:9]1[N:10]=[C:11]([C:14]([O:16][CH3:17])=[O:15])[C:12]([NH:8][C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)=[N:13]1)[CH3:24]

Participants

4

Reactant 2

HCID 669183-Chloropropyl(diethyl)amineHCID 13135871HCID 13135871, compound

Product 1

HCID 13135892HCID 13135892, compoundYield 27.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture consisting of 5.1 gm (0.02 mol) of methyl 1-(4-chlorophenyl)-5-amino-1H-1,2,3-triazole-4-carboxylate, 100 ml of absolute dimethyl formamide and 7.5 gm (0.05 mol) of 1-chloro-3-diethylamino-propane was reacted analogous to Example 1, the reaction mixture was evaporated in vacuo, the residue was dissolved in 2N hydrochloric acid, and the solution was fractionally extracted with ether at stepwisely increasing pH values. After evaporation of the ether phases which were shown to be identical and pure by thin-layer chromatography, the residue was dissolved in ethyl acetate, and the hydrochloride was precipitated with ethereal hydrochloric acid and recrystallized twice, yielding 1.1 gm of the desired compound, corresponding to 13.7% of theory; melting point 181° C.

Workup

  1. customwas reacted analogous to Example 1
  2. customthe reaction mixture was evaporated in vacuo
  3. dissolutionthe residue was dissolved in 2N hydrochloric acid
  4. extractionthe solution was fractionally extracted with ether
  5. temperatureat stepwisely increasing pH values
  6. customAfter evaporation of the ether phases which
  7. dissolutionthe residue was dissolved in ethyl acetate
  8. customthe hydrochloride was precipitated with ethereal hydrochloric acid
  9. customrecrystallized twice

Sources & evidence

ORD record
ord-65504ce464ac4bcea700e6fa8e83726c
Source dataset
uspto-grants-1985_03
Patent number
US04505912

Reaction notes

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