2,2-Diethoxyethylamine → HCID 178467944, compound

HRID 596880Notes

Reaction equation

HRID 596880 reaction equation
[ClH:1].[N+:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[O:15][C:14]([C:16](=[NH:20])OCC)=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)([O-:4])=[O:3].[CH2:21]([O:23][CH:24]([O:27][CH2:28][CH3:29])[CH2:25][NH2:26])[CH3:22]>C(O)C>[ClH:1].[CH2:21]([O:23][CH:24]([O:27][CH2:28][CH3:29])[CH2:25][NH:26][C:16]([C:14]1[O:15][C:11]([C:8]2[CH:7]=[CH:6][C:5]([N+:2]([O-:4])=[O:3])=[CH:10][CH:9]=2)=[CH:12][CH:13]=1)=[NH:20])[CH3:22]

Participants

4

Reactant 2

HCID 695242,2-DiethoxyethylamineHCID 21436379HCID 21436379, compound

Product 1

HCID 178467944HCID 178467944, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 98 g (0.33 mole) of ethyl 5-(4-nitrophenyl)-2-furimidate hydrochloride and 48 g (0.36 mole) of aminoacetaldehyde diethyl acetal in 1500 ml of absolute ethanol was heated under reflux for 4 hr. After standing in a refrigerator for 2 days, the solid which was deposited was collected by filtration and washed with anhydrous ether to give 38 g (30%) of N-(2,2-diethoxyethyl)-5-(4-nitrophenyl)-2-furamidine hydrochloride. The filtrate was concentrated on a rotary evaporator. The solid which was deposited was collected by filtration and washed with anhydrous ether to give 34 g (57% total yield) of additional product, m.p. 220°-280° (dec.)

Workup

  1. temperatureunder reflux for 4 hr
  2. filtrationthe solid which was deposited was collected by filtration
  3. washwashed with anhydrous ether

Sources & evidence

ORD record
ord-0dad4f11b5484d1d993a144105e91a33
Source dataset
uspto-grants-1977_03
Patent number
US04012414

Reaction notes

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