Diethylaminoethyl chloride → HCID 13135898, compound

HRID 2164538Notes

Reaction equation

HRID 2164538 reaction equation
[F: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:18][CH2:19][CH2:20][N:21]([CH2:24][CH3:25])[CH2:22][CH3:23]>CN(C)C=O>[ClH:18].[CH2:20]([N:21]([CH2:24][CH3:25])[CH2:22][CH2:23][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]([F:1])=[CH:3][CH:4]=2)=[N:13]1)[CH3:19]

Participants

4

Reactant 2

HCID 13364Diethylaminoethyl chlorideHCID 11837271HCID 11837271, compound

Product 1

HCID 13135898HCID 13135898, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture consisting of 4.7 gm (0.02 mol) of methyl 1-(4-fluorophenyl)-5-amino-1H-1,2,3-triazole-4-carboxylate, 70 ml of absolute dimethyl formamide and 8.1 gm (0.06 mol) of 1-chloro-2-diethylamino-ethane was reacted as in Example 1. The reaction mixture was then evaporated in vacuo and the residue was dissolved in 2N hydrochloric acid. The solution was extracted with chloroform, filtered through activated charcoal, dried over sodium sulfate, and the chloroform was distilled off in vacuo. After recrystallization from isopropanol, 1.5 gm (20.2% of theory) of the desired compound were obtained; melting point 179° C.

Workup

  1. customwas reacted as in Example 1
  2. customThe reaction mixture was then evaporated in vacuo
  3. dissolutionthe residue was dissolved in 2N hydrochloric acid
  4. extractionThe solution was extracted with chloroform
  5. filtrationfiltered through activated charcoal
  6. dry with materialdried over sodium sulfate
  7. distillationthe chloroform was distilled off in vacuo
  8. customAfter recrystallization from isopropanol, 1.5 gm (20.2% of theory) of the desired compound
  9. customwere obtained

Sources & evidence

ORD record
ord-5382f7cc556a40d2b1e0becbfa7327a3
Source dataset
uspto-grants-1985_03
Patent number
US04505912

Reaction notes

Loading…