Diethylamine → HCID 20351843, compound

HRID 371866Notes

Reaction equation

HRID 371866 reaction equation
[NH:1]([C:5]1[CH:12]=[CH:11][C:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:9][C:6]=1[CH2:7]Br)[C:2]([CH3:4])=[O:3].[CH2:18]([NH:20][CH2:21][CH3:22])[CH3:19]>C(Cl)(Cl)Cl.C(O)C>[NH:1]([C:5]1[CH:12]=[CH:11][C:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:9][C:6]=1[CH2:7][N:20]([CH2:21][CH3:22])[CH2:18][CH3:19])[C:2]([CH3:4])=[O:3]

Participants

5

Reactant 2

HCID 8021DiethylamineHCID 20319099HCID 20319099, compound

Product 1

HCID 20351843HCID 20351843, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6212ChloroformSolvent

Procedure

30 gm of 2-acetamino-5-carbethoxy-benzyl bromide were dissolved in a mixture of 400 ml of chloroform and 100 ml of ethanol, and the solution was refluxed with 22 gm of diethylamine for 1 hour. Thereafter, the reaction solution was cooled, then evaporated in vacuo, the residue was distributed between a mixture of dilute ammonia and chloroform, and the chloroform phase was dried over sodium sulfate and evaporated in vacuo. The residue was purified by chromatography on silicagel (elution agent: ethyl acetate) and recrystallized from ethanol, yielding 2-acetamino-5-carbethoxy-N,N-diethyl-benzylamine, m.p. 57-59° C.

Workup

  1. temperatureThereafter, the reaction solution was cooled
  2. customevaporated in vacuo
  3. additionthe residue was distributed between a mixture of dilute ammonia and chloroform
  4. dry with materialthe chloroform phase was dried over sodium sulfate
  5. customevaporated in vacuo
  6. customThe residue was purified by chromatography on silicagel (elution agent: ethyl acetate)
  7. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-fe991ffab51e432baad1d7d41f3cc849
Source dataset
uspto-grants-1978_05
Patent number
USRE029628

Reaction notes

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