Ethanol → HCID 67315765, compound

HRID 1012583Notes

Reaction equation

HRID 1012583 reaction equation
CC1O[C:5]([CH:7]=O)=[CH:4][CH:3]=1.C(N(CCC)[CH2:13][CH2:14][CH2:15][CH2:16][NH:17][CH2:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23][NH2:24])=[CH:21][CH:20]=1)CC.S([O-])([O-])(=O)=O.[Na+].[Na+].[CH2:37]([OH:39])[CH3:38]>>[CH2:16]([N:17]([CH2:18][CH2:19][CH3:20])[CH2:7][CH2:5][CH2:4][CH2:3][CH:23]([NH2:24])[C:22]1[CH:21]=[CH:20][C:19]([CH2:18][N:17]=[CH:16][C:15]2[O:39][C:37]([CH3:38])=[CH:13][CH:14]=2)=[CH:26][CH:25]=1)[CH2:15][CH3:14]

Participants

5

Reactant 4

HCID 702EthanolHCID 120975-MethylfurfuralHCID 24436Sodium SulfateHCID 59850548HCID 59850548, compound

Product 1

HCID 67315765HCID 67315765, compoundYield 100%

Procedure

Under a nitrogen stream 415 mg (3.77 mmol, 1.1 equivalents) of 5-methyl-2-furaldehyde, 10 ml of ethanol, 1.0 g (3.43 mmol, 1.0 equivalent) of 4-[(4-dipropylaminobutyl)amino]methylbenzylamine (5a), and 3 g of anhydrous sodium sulfate were charged in a 50 ml recovery flask and reacted at 25° C. for 20 hours. After completion of the reaction, the reaction solution was filtered, and concentrated, thereby obtaining 1.32 g of {(4-dipropylaminobutyl)-[4-(5-methylfuran-2-ylmethylidene)aminomethylbenzyl]}amine (26) as a reddish brown oily substance (yield: 100%). [HPLC: 95.7% (HPLC measurement conditions C)]

Workup

  1. customreacted at 25° C. for 20 hours
  2. customAfter completion of the reaction
  3. filtrationthe reaction solution was filtered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-94d247d4936d46aaa58b131434f48581
Source dataset
uspto-grants-2011_07
Patent number
US07977512B2

Reaction notes

Loading…