(2,2-Diethoxyethyl)dimethylamine → HCID 131711015, compound

HRID 1833420Notes

Reaction equation

HRID 1833420 reaction equation
[CH2:1]([O:3][CH:4]([O:9][CH2:10][CH3:11])[CH2:5][N:6]([CH3:8])[CH3:7])[CH3:2].[N+:12]([C:15]1[CH:20]=[CH:19][C:18]([C:21]2[O:25][C:24]([C:26]([CH2:28][Cl:29])=[O:27])=[CH:23][CH:22]=2)=[CH:17][CH:16]=1)([O-:14])=[O:13]>C(O)C>[OH2:3].[Cl-:29].[CH2:10]([O:9][CH:4]([O:3][CH2:1][CH3:2])[CH2:5][N+:6]([CH3:7])([CH3:8])[CH2:28][C:26]([C:24]1[O:25][C:21]([C:18]2[CH:19]=[CH:20][C:15]([N+:12]([O-:14])=[O:13])=[CH:16][CH:17]=2)=[CH:22][CH:23]=1)=[O:27])[CH3:11].[CH2:10]([O:9][CH:4]([O:3][CH2:1][CH3:2])[CH2:5][N+:6]([CH2:28][C:26]([C:24]1[O:25][C:21]([C:18]2[CH:19]=[CH:20][C:15]([N+:12]([O-:14])=[O:13])=[CH:16][CH:17]=2)=[CH:22][CH:23]=1)=[O:27])([CH3:7])[CH3:8])[CH3:11].[Cl-:29]

Participants

4

Reactant 2

HCID 77163(2,2-Diethoxyethyl)dimethylamineHCID 213893612-Chloro-1-[5-(4-nitrophenyl)furan-2-yl]ethan-1-one

Product 1

HCID 131711015HCID 131711015, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Dimethylaminoacetaldehyde diethyl acetal (29 g, 0.18 mole) was added dropwise to a stirred mixture of 40 g (0.15 mole) of chloromethyl 5-(4-nitrophenyl)-2-furyl ketone in 750 ml of absolute ethanol at 30° over 15 minutes. The mixture was heated under reflux for 22 hrs and was filtered hot to remove a black insoluble material. The filtrate was cooled in ice, and the brown solid was filtered and discarded. The filtrate was diluted with 1.5 liters of anhydrous ether, and the solid which was deposited was collected by filtration to give 45 g (69%) of (2,2-diethoxyethyl)dimethyl[5-(4-nitrophenyl)-2-furoylmethyl] ammonium chloride hemihydrate. Two recrystallizations from CH3CN gave an analytical sample, m.p. 113°-118°.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 22 hrs
  3. filtrationwas filtered hot
  4. customto remove a black insoluble material
  5. temperatureThe filtrate was cooled in ice
  6. filtrationthe brown solid was filtered
  7. additionThe filtrate was diluted with 1.5 liters of anhydrous ether
  8. filtrationthe solid which was deposited was collected by filtration

Sources & evidence

ORD record
ord-3f0a2f3dd4d74a18ab0a46df57df333f
Source dataset
uspto-grants-1978_01
Patent number
US04066671

Reaction notes

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