2-Chloro-N,N-dimethylethylamine → HCID 13135884, compound

HRID 2164536Notes

Reaction equation

HRID 2164536 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][CH2:17][CH2:18][CH2:19][CH3:20])=[O:15])[N:10]=[N:9]2)=[CH:4][CH:3]=1.Cl[CH2:22][CH2:23][N:24]([CH3:26])[CH3:25]>CN(C)C=O>[ClH:1].[CH3:25][N:24]([CH3:26])[CH2:23][CH2:22][N:9]1[N:10]=[C:11]([C:14]([O:16][CH2:17][CH2:18][CH2:19][CH3:20])=[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

Participants

4

Reactant 2

HCID 79012-Chloro-N,N-dimethylethylamineHCID 13135870Butyl 5-amino-1-(4-chlorophenyl)-1H-1,2,3-triazole-4-carboxylate

Product 1

HCID 13135884HCID 13135884, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture consisting of 6.0 gm (0.02 mol) of n-butyl 1-(4-chlorophenyl)-5-amino-1H-1,2,3-triazole-4-carboxylate, 100 ml of absolute dimethylformamide and 4.3 gm (0.04 mol) of 1-chloro-2-dimethylamino-ethane was reacted as in Example 1, the reaction mixture was evaporated, the residue was dissolved in 2N hydrochloric acid and water, and the solution was extracted with ether at stepwisely increasing pH values. After evaporation of those ether phases shown to be pure by thin-layer chromatography, the residue was dissolved in a little isopropanol, the solution was acidified with ethereal hydrochloric acid, and the hydrochloride was precipitated with ethyl acetate. After recrystallization from ethanol, 0.8 gm of the desired compound, corresponding to 9.9% of theory, was obtained with a melting point of 171° C.

Workup

  1. customwas reacted as in Example 1
  2. customthe reaction mixture was evaporated
  3. dissolutionthe residue was dissolved in 2N hydrochloric acid
  4. extractionwater, and the solution was extracted with ether
  5. temperatureat stepwisely increasing pH values
  6. customAfter evaporation of those ether phases
  7. dissolutionthe residue was dissolved in a little isopropanol
  8. customthe hydrochloride was precipitated with ethyl acetate
  9. customAfter recrystallization from ethanol, 0.8 gm of the desired compound
  10. customcorresponding to 9.9% of theory, was obtained with a melting point of 171° C.

Sources & evidence

ORD record
ord-45dc5dcbe870449b82584f302b1a7eb2
Source dataset
uspto-grants-1985_03
Patent number
US04505912

Reaction notes

Loading…