Diethylamine → HCID 20351843, compound

HRID 435837Notes

Reaction equation

HRID 435837 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 silica gel (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 silica gel (elution agent: ethyl acetate)
  7. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-9d84739c341647e2b3e9c22583a7f793
Source dataset
uspto-grants-1977_02
Patent number
US04006246

Reaction notes

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