1-Butanol → HCID 89655515, compound

HRID 1395946Notes

Reaction equation

HRID 1395946 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][C:21](=[O:24])[CH:22]=[CH2:23])[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>[C: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][C:16](=[O:20])[CH:17]=[CH2:18])[C:5]=1[OH:6])(=[O:24])[CH:22]=[CH2:23]

Participants

5

Reactant 3

HCID 2631-ButanolHCID 17913Squaric acidHCID 89656182HCID 89656182, compound

Product 1

HCID 89655515HCID 89655515, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

342 mg of squaric acid and 2.12 g of 2-(methyl(3-acryloxyphenyl)amino)ethan-1-ol were 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 hours. Next, a Dean-Stark trap set was used to remove water generated during the reaction and kept being reacted. When the reaction was complete, the reactant was cooled down, producing crystals. The crystals were filtered, several times cleaned with hexane, and once more recrystallized, obtaining a desired compound.

Workup

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

Sources & evidence

ORD record
ord-07bc462f17ac4e93b274bb770155c413
Source dataset
uspto-grants-2014_12
Patent number
US08900780B2

Reaction notes

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