Water → HCID 178524080, compound

HRID 1875302Notes

Reaction equation

HRID 1875302 reaction equation
[CH2:1]1[C:11]2[C:12]3[C:3](=[CH:4][CH:5]=[C:6]4[C:16](=[O:17])[O:15][C:13](=[O:14])[C:8](=[CH:9][CH:10]=2)[C:7]4=3)[CH2:2]1.[CH:18]1([NH2:24])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1.O>CC(N(C)C)=O>[CH:18]1([N:24]=[C:16]([C:6]2[C:7]3=[C:12]4[C:3]([CH2:2][CH2:1][C:11]4=[CH:10][CH:9]=[C:8]3[C:13]([OH:15])=[O:14])=[CH:4][CH:5]=2)[OH:17])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

5

Reactant 3

HCID 962WaterHCID 7965CyclohexylamineHCID 4669379HCID 4669379, compound

Product 1

HCID 178524080HCID 178524080, compoundYield 98.5%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
157.5 °C

Procedure

A slurry of 5,6-acenaphthenedicarboxylic acid anhydride (33.6 g, 0.150 mol) (B. M. Trost, G. Michael Bright, Charles Frihart, and David Brittelli, Journal of the American Chemical Society, 93(3), 737-45 (1971); James J. Jordan, Jr; U.S. Pat. No. 3,935,226) in 175 ml of DMAc was treated with cyclohexylamine (34.2 ml, 0.300 mol) over one minute and a thick paste formed. This mixture was heated at 155-160° C. for 2 hours. The resulting deep green solution was poured into 2 liters of water. The mixture was stirred for 10 minutes and then was filtered. The accumulated solid was washed with water and air-dried to provide a yellow solid (45.1 g, 98.5%), mp 264-265° C. A portion (2.00 g) of this material was recrystallized from a mixture of n-propyl acetate and heptanes (200 ml, 1:1 v/v) to provide fine yellow needles (1.42 g, 70%), mp 266-267° C. Anal. Calcd for C20H19NO2: C, 78.66; H, 6.27; N, 4.59. Found C, 78.39; H, 6.15; N, 4.83.

Workup

  1. customa thick paste formed
  2. filtrationwas filtered
  3. washThe accumulated solid was washed with water
  4. customair-dried

Sources & evidence

ORD record
ord-2a18d1ce9c314cb3b3d252b241c98d54
Source dataset
uspto-grants-2012_11
Patent number
US08309394B2

Reaction notes

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