Iodoethane → HCID 22153308, compound

HRID 1111090Notes

Reaction equation

HRID 1111090 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[NH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][OH:17].C(=O)([O-])[O-].[K+].[K+].[CH2:24](I)[CH3:25]>CS(C)=O>[OH:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][N:10]([C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1)[CH2:24][CH3:25]

Participants

6

Reactant 4

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 199606-Amino-1-hexanolHCID 680234-Fluorobenzaldehyde2×

Product 1

HCID 22153308HCID 22153308, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
95 °C

Procedure

To a three-neck flask fitted with a mechanical stirrer, a thermometer, and a condenser is added 124.0 g (1 mole) of 4-fluorobenzaldehyde, 117.2 g (1 mole) of 6-amino-1-hexanol, 276.4 g (2 mole) of potassium carbonate, and dimethylsulfoxide. The reaction mixture is heated at 95° C. for about 3 hours until thin-layer chromatography indicates no more 4-fluorobenzaldehyde is present After cooling to room temperature, 156 g (1 mole) of ethyl iodide is added dropwise, and the reaction is stirred at room temperature for 5 hours The solution is poured into a four-fold excess of ice water, and the solid product is collected by filtration and purified by recrystallization from water.

Workup

  1. customTo a three-neck flask fitted with a mechanical stirrer
  2. temperatureAfter cooling to room temperature
  3. filtrationthe solid product is collected by filtration
  4. custompurified by recrystallization from water

Sources & evidence

ORD record
ord-de84238f5ad74c3192342d297beb8574
Source dataset
uspto-grants-1990_12
Patent number
US04978476

Reaction notes

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