Phthalic Anhydride → HCID 68687024, compound

HRID 1169852Notes

Reaction equation

HRID 1169852 reaction equation
Cl.[NH2:2][C:3]1(O)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.[CH2:10](N(CC)CC)C.[C:17]1(=O)[O:22][C:20](=[O:21])[C:19]2=[CH:23][CH:24]=[CH:25][CH:26]=[C:18]12>C1(C)C=CC=CC=1>[CH2:10]=[C:6]1[CH2:7][CH2:8][CH:3]([N:2]2[C:20](=[O:21])[C:19]3[C:18](=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:17]2=[O:22])[CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 6811Phthalic AnhydrideHCID 8471TriethylamineHCID 21877166HCID 21877166, compound

Product 1

HCID 68687024HCID 68687024, compoundYield 84.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
125 °C

Procedure

Aminocyclohexanol hydrochloride (6.3 g, 41.6 mmol) and triethylamine (11.6 mL, 83.1 mmol) were stirred in toluene (150 mL) at room temperature for 1 hour. To this was added phthalic anhydride (7.4 g, 49.9 mmol) and the reaction mixture was stirred at 120-130° C. The by-product water was removed from the reaction mixture. Toluene was concentrated under reduced pressure. The crude compound thus obtained was purified by column chromatography using ether in hexane solvent mixture (2:1) as eluent to furnish the title compound (8.5 g, 84%).

Workup

  1. customThe by-product water was removed from the reaction mixture
  2. concentrationToluene was concentrated under reduced pressure
  3. customThe crude compound thus obtained
  4. customwas purified by column chromatography

Sources & evidence

ORD record
ord-9440f8d1783946a1b538d013ddc83fb8
Source dataset
uspto-grants-2010_11
Patent number
US07825147B2

Reaction notes

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