Furfurylamine → HCID 86753401, compound

HRID 618415Notes

Reaction equation

HRID 618415 reaction equation
[CH2:1]([NH2:7])[C:2]1[O:6][CH:5]=[CH:4][CH:3]=1.[C:8](O)(=O)[CH2:9][O:10][CH2:11][CH2:12][O:13][CH2:14][CH2:15][O:16][C:17](O)=O.[C:22]1(C)C(C)=CC=CC=1>>[CH2:1]([N-:7][CH2:22][C:14]1[O:13][CH:12]=[CH:11][CH:15]=1)[C:2]1[O:6][CH:5]=[CH:4][CH:3]=1.[CH3:8][CH2:9][O:10][CH2:11][CH2:12][O:13][CH2:14][CH2:15][O:16][CH3:17]

Participants

4

Reactant 3

HCID 3438FurfurylamineHCID 7237O-XyleneHCID 22340213HCID 22340213, compound

Product 1

HCID 86753401HCID 86753401, compoundYield 87%

Conditions

Temperature
180 °C

Procedure

Furfuryl amine (19.9 grams) and 3,6,9-trioxadecanedioic acid (obtained from Hoechst Celanese Company, 22.6 grams) were added to xylene (130 milliliters) in a 500 milliliter flask fitted with condenser, Dean Stark water removal trap, overhead stirrer and oil bath heated to about 180° C. The mixture was stirred under reflux for 2.3 hours, during which time 3.45 milliliters of water were collected in the Dean Stark trap (94 percent). The mixture was cooled to room temperature with stirring, and the solvent removed at reduced pressure on a rotary evaporator to yield 3,6,9-trioxadecane difurfurylamide as a slightly brownish viscous oil (38.7 grams; 87 percent yield). Infrared spectroscopy verified the absence of acid carboxyl groups from the starting material.

Workup

  1. customfitted with condenser
  2. customDean Stark water removal trap, overhead stirrer and oil bath
  3. temperatureunder reflux for 2.3 hours, during which time 3.45 milliliters of water
  4. customwere collected in the Dean Stark trap (94 percent)
  5. temperatureThe mixture was cooled to room temperature
  6. stirringwith stirring
  7. customthe solvent removed at reduced pressure on a rotary evaporator

Sources & evidence

ORD record
ord-5a79d9c6391e4811a05b6b9dbe5a6c39
Source dataset
uspto-grants-1999_09
Patent number
US05952402

Reaction notes

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