1-Butanol → HCID 89655416, compound

HRID 1395944Notes

Reaction equation

HRID 1395944 reaction equation
[C:1]1(O)[C:5](=[O:6])[C:3](=O)[C:2]=1[OH:7].[CH3:9][N:10]([C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH:15]=1)[CH2:11][CH2:12][OH:13].[CH3:25][CH2:26][CH2:27][CH2:28][OH:29]>C1(C)C=CC=CC=1>[CH2:21]([O:20][C:16]1[CH:15]=[C:14]([N:10]([CH2:11][CH2:12][OH:13])[CH3:9])[CH:19]=[CH:18][C:17]=1[C:3]1[C:2]([OH:7])=[C:1]([C:27]2[CH:26]=[CH:25][C:14]([N:10]([CH2:11][CH2:12][OH:13])[CH3:9])=[CH:15][C:28]=2[O:29][CH2:19][CH2:18][CH2:17][CH3:16])[C:5]=1[OH:6])[CH2:22][CH2:23][CH3:24]

Participants

5

Reactant 3

HCID 2631-ButanolHCID 17913Squaric acidHCID 89655288HCID 89655288, compound

Product 1

HCID 89655416HCID 89655416, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

342 mg of squaric acid and 2.14 g of 2-(methyl(3-butoxyphenyl)amino)ethan-1-ol was put in a 100 mL 3-necked round bottom flask, and 40 mL of n-BuOH and 20 mL of toluene were added thereto. The mixture was heated and refluxed at 120° C. for 7 hour. Then, a Dean-Stark trap set was used to remove water generated from the reactant during the reaction and kept being reacted. When the reaction was complete, the reactant was cooled down, producing crystals. The crystals was filtered, several times washed with hexanes, and once more recrystallized, obtaining a desired compound.

Workup

  1. temperatureThe mixture was heated
  2. customto remove water
  3. customgenerated from the reactant during the reaction
  4. customkept being reacted
  5. temperaturethe reactant was cooled down
  6. customproducing crystals
  7. filtrationThe crystals was filtered
  8. washseveral times washed with hexanes
  9. customonce more recrystallized

Sources & evidence

ORD record
ord-7c25bd8d1ac84b2f9b71eb142266dcbf
Source dataset
uspto-grants-2014_12
Patent number
US08900780B2

Reaction notes

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