1-Butanol → HCID 89656232, compound

HRID 1395943Notes

Reaction equation

HRID 1395943 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]([NH:20][C:21]([CH3:23])=[O:22])[CH:15]=1)[CH2:11][CH2:12][OH:13].[CH3:24][CH2:25][CH2:26][CH2:27]O>C1(C)C=CC=CC=1>[NH: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:24]([N:10]([CH2:11][CH2:12][OH:13])[CH3:9])=[CH:15][C:16]=2[NH:20][C:21]([CH3:23])=[O:22])[C:5]=1[OH:6])[C:21]([CH3:23])=[O:22]

Participants

5

Reactant 3

HCID 2631-ButanolHCID 17913Squaric acidHCID 23325744HCID 23325744, compound

Product 1

HCID 89656232HCID 89656232, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

342 mg of squaric acid) and 2 g of 2-(methyl(3-acetaminophenyl)amino)ethan-1-ol were put in a 100 mL 3-neck rounded 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 10 hours. Then, a Dean-Stark trap set was used to remove water generated from the reactant during the reaction, and the reactant 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 from the reactant during the reaction
  4. customthe reactant kept 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-f20999db59ab4d6091d7d696ee33cec5
Source dataset
uspto-grants-2014_12
Patent number
US08900780B2

Reaction notes

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