Formic Acid → HCID 54020778, compound

HRID 563914Notes

Reaction equation

HRID 563914 reaction equation
[CH:1]([OH:3])=O.[CH2:4]([O:6][CH2:7][CH2:8][CH2:9][NH2:10])[CH3:5].C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1>[CH2:4]([O:6][CH2:7][CH2:8][CH2:9][NH:10][CH:1]=[O:3])[CH3:5]

Participants

5

Reactant 3

HCID 284Formic AcidHCID 11430Potassium CarbonateHCID 22720Propanolamine ethyl ether

Product 1

HCID 54020778HCID 54020778, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Formic acid (9.4 mL, 0.208×1.2 mol) was added to a toluene (250 mL) solution of 3-ethoxypropylamine (25 mL, 0.208 mol) at room temperature, and heated under reflux for 17 hours while removing water formed as a by-product with a Dean-Stark tube. After cooling to room temperature, K2CO3 (14 g, 0.208×0.5 mol) was added and it was stirred for 90 minutes. Insoluble materials were removed by filtration, washed with toluene, and the filtrate was concentrated to dryness. The residue was purified by vacuum distillation with a Vigreux fractionating column (15 cm) (fraction at 0.6 kpa, 114° C. to 115° C. collected), and N-(3-ethoxypropyl)formamide (21.79 g, 0.166 mol, 80%) was obtained as a colorless transparent liquid.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 17 hours
  3. customwhile removing water
  4. customformed as a by-product with a Dean-Stark tube
  5. customInsoluble materials were removed by filtration
  6. washwashed with toluene
  7. concentrationthe filtrate was concentrated to dryness
  8. distillationThe residue was purified by vacuum distillation with a Vigreux fractionating column (15 cm) (fraction at 0.6 kpa, 114° C. to 115° C. collected)

Sources & evidence

ORD record
ord-f51984bb6c884bdf83a8cf5c9a559d00
Source dataset
uspto-grants-2011_11
Patent number
US08067595B2

Reaction notes

Loading…