Ethanolamine → HCID 19598464, compound

HRID 724745Notes

Reaction equation

HRID 724745 reaction equation
[CH2:1]([CH2:3][NH2:4])[OH:2].[O:5]=[C:6]1[C:11]2[CH:12]=[CH:13]O[C:10]=2[CH2:9][CH2:8][CH2:7]1.C(OC(C)C)(C)C>C(O)C>[O:5]=[C:6]1[CH2:7][CH2:8][CH2:9][C:10]2[N:4]([CH2:3][CH2:1][OH:2])[CH:13]=[CH:12][C:11]1=2

Participants

5

Reactant 3

HCID 700EthanolamineHCID 7914Diisopropyl EtherHCID 27335414,5,6,7-Tetrahydro-1-benzofuran-4-one

Product 1

HCID 19598464HCID 19598464, compoundYield 83.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
130 °C

Procedure

80 g of ethanolamine were added to a solution of 136 g of 4-oxo-4,5,6,7-tetrahydrobenzofuran in 250 cm3 of ethanol. The solution was heated at 130° C. for 6 hours. After allowing the reaction mixture to return to room temperature with stirring, the mixture was poured over a mixture of 800 cm3 of isopropyl ether and 200 cm3 of petroleum ether. A product crystallized with stirring, and then it was drained, washed with petroleum ether and dried under vacuum over phosphorus pentoxide. 160 g of the expected product was recovered, which product was recrystallized from 240 cm3 of isopropanol. 150 g of the expected product was obtained whose melting point ranged from 96° to 97° C.

Workup

  1. customto return to room temperature
  2. customA product crystallized
  3. stirringwith stirring
  4. washwashed with petroleum ether
  5. dry with materialdried under vacuum over phosphorus pentoxide
  6. custom160 g of the expected product was recovered
  7. customwhich product was recrystallized from 240 cm3 of isopropanol

Sources & evidence

ORD record
ord-b9eb90dc679544069e953154e50a90e9
Source dataset
uspto-grants-1998_01
Patent number
US05704948

Reaction notes

Loading…