Triethylamine → HCID 22501920, compound

HRID 1633992Notes

Reaction equation

HRID 1633992 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[O:12])[O:10][C:8](=O)[C:7]2=[CH:13][CH:14]=1)([O-:3])=[O:2].[CH:15]1([NH2:18])[CH2:17][CH2:16]1.C(N(CC)CC)C.C(N=C=NC(C)C)(C)C>C1COCC1.CN(C=O)C>[CH:15]1([N:18]2[C:11](=[O:12])[C:6]3=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:14][CH:13]=[C:7]3[C:8]2=[O:10])[CH2:17][CH2:16]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 12734DiisopropylcarbodiimideHCID 69828CyclopropylamineHCID 2309764-Nitrophthalic acid anhydride

Product 1

HCID 22501920HCID 22501920, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

4-Nitrophthalic anhydride (5.60 g, 28.9 mmol) was dissolved in THF (50 mL), and cyclopropylamine (2.10 mL, 30 mmol) was added slowly while stirring under an inert atmosphere. After 30 min, a suspension was obtained. Triethylamine (8.2 mL, 60 mmol) and diisopropylcarbodiimide (5.50 mL, 35 mmol) were added followed by DMF (100 mL). The reaction mixture was then heated to 70° C. for 48 hours. The mixture was cooled to room temperature and the reaction volume was reduced to one-tenth of the original volume by rotary evaporation in vacuo. The precipitated N,N′-diisopropylurea was removed by filtration, and water (40 mL) was added to the mother liquor resulting in formation of a precipitate. The precipitate was collected by filtration and dried overnight in a vacuum oven to give 6.02 g (90%) of N-cyclopropyl-4-nitrophthalimide.

Workup

  1. customa suspension was obtained
  2. temperatureThe mixture was cooled to room temperature
  3. customthe reaction volume was reduced to one-tenth of the original volume by rotary evaporation in vacuo
  4. customThe precipitated N,N′-diisopropylurea was removed by filtration, and water (40 mL)
  5. additionwas added to the mother liquor
  6. customresulting in formation of a precipitate
  7. filtrationThe precipitate was collected by filtration
  8. customdried overnight in a vacuum oven

Sources & evidence

ORD record
ord-55c82d4e839b44c2b56ee2b1e0e59eac
Source dataset
uspto-grants-2003_01
Patent number
US06503949B1

Reaction notes

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