N-(2-aminoethyl)acetamide → HCID 14235033, compound

HRID 2249193Notes

Reaction equation

HRID 2249193 reaction equation
CO[CH:3]1[CH:7]([CH:8]=[O:9])[CH2:6][CH:5](OC)O1.[C:12]([NH:15][CH2:16][CH2:17][NH2:18])(=[O:14])[CH3:13].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>>[C:12]([NH:15][CH2:16][CH2:17][N:18]1[CH:5]=[CH:6][C:7]([CH:8]=[O:9])=[CH:3]1)(=[O:14])[CH3:13]

Participants

5

Reactant 4

HCID 66082N-(2-aminoethyl)acetamideHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 567310Tetrahydro-2,5-dimethoxyfuran-3-carbaldehyde

Product 1

HCID 14235033HCID 14235033, compound

Conditions

Temperature
80 °C

Procedure

8.5 g (0.053 mol) of 2,5-dimethoxytetrahydrofuran-3-aldehyde and 5.4 g (0.053 mol) of 2-(acetylamino)-ethylamine are stirred at 60° C. for 1 hour. After addition of 0.05 g of p-toluenesulphonic acid hydrate, the mixture is stirred at 80° C. for 90 minutes and cooled, sodium bicarbonate solution is added and the mixture is extracted with methylene chloride and then with pentanol. The organic phases are concentrated and chromatographed over a silica gel column with methylene chloride/methanol =95:5 as the mobile phase. The product isolated is crystallized from ethyl acetate/ligroin.

Workup

  1. temperaturecooled
  2. extractionthe mixture is extracted with methylene chloride
  3. concentrationThe organic phases are concentrated
  4. customchromatographed over a silica gel column with methylene chloride/methanol =95:5 as the mobile phase
  5. customThe product isolated
  6. customis crystallized from ethyl acetate/ligroin

Sources & evidence

ORD record
ord-e28a67eca1594495bf06308bf10995c0
Source dataset
uspto-grants-1991_08
Patent number
US05043348

Reaction notes

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