Potassium Carbonate → 3-Phenyl-1-oxa-2,4-diaza-spiro[4.4]non-2-en4-ylamine

HRID 1184304Notes

Reaction equation

HRID 1184304 reaction equation
C([O-])([O-])=O.[K+].[K+].[C:7]1(=[N:12][NH2:13])[CH2:11][CH2:10][CH2:9][CH2:8]1.[C:14](Cl)(=[N:21][OH:22])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>O.C(Cl)Cl>[C:15]1([C:14]2[N:12]([NH2:13])[C:7]3([CH2:11][CH2:10][CH2:9][CH2:8]3)[O:22][N:21]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 253276CyclopentylidenehydrazineHCID 2756315N-hydroxybenzenecarboximidoyl chloride

Product 1

HCID 146846683-Phenyl-1-oxa-2,4-diaza-spiro[4.4]non-2-en4-ylamineYield 50,341.301%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent3×

Procedure

A round bottom flask was charged with a solution of 20 g of K2CO3 in 50 mL of water and cooled in an ice bath. Cyclopentylidene-hydrazine (7.9 g, 80 mmol) in 25 mL of CH2Cl2 was added, followed by a drop-wise addition of benzohydroximoyl chloride (5 g, 0.032 mmol) in 25 mL of CH2Cl2 over a period of 15 minutes. The mixture was stirred for several days, and allowed to warm to room temperature. Water (50 mL) and CH2Cl2 (50 mL) were added and the phases were separated. The organic layer was washed twice with 50 mL of water, dried over MgSO4, and filtered. The solvent was removed in vacuo, leaving 9 g of a waxy solid. Crystallization from ethyl acetate/hexane provided 3.5 g (50%) of 3-phenyl-1-oxa-2,4-diaza-spiro[4,4]non-2-en-4-ylamine after drying. 1H-NMR (300 MHz, CDCl3) δ (ppm): 7.72 ((m, 2H), 7.46 (m, 3H), 3.54 (s, 2H), 2.1 (m, 2H), 2.0 (m, 2H), 1.85 (m, 2H), 1.8 (m, 2H).

Workup

  1. temperaturecooled in an ice bath
  2. customthe phases were separated
  3. washThe organic layer was washed twice with 50 mL of water
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customThe solvent was removed in vacuo
  7. customleaving 9 g of a waxy solid
  8. customCrystallization from ethyl acetate/hexane

Sources & evidence

ORD record
ord-3b05d918449a4a71a39c2d89b003c072
Source dataset
uspto-grants-2014_03
Patent number
US08669072B2

Reaction notes

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