Dimethylformamide → 3-(2-Chloro-4-nitrophenyl)-1,3-diazaspiro[4.6]undecane-2,4-dione

HRID 1625110Notes

Reaction equation

HRID 1625110 reaction equation
[NH2:1][C:2]1([C:9]([OH:11])=O)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.CN(C=O)C.C1CCN2C(=NCCC2)CC1.[Cl:28][C:29]1[CH:34]=[C:33]([N+:35]([O-:37])=[O:36])[CH:32]=[CH:31][C:30]=1[N:38]=[C:39]=[O:40]>ClCCCl.C(Cl)Cl>[Cl:28][C:29]1[CH:34]=[C:33]([N+:35]([O-:37])=[O:36])[CH:32]=[CH:31][C:30]=1[N:38]1[C:9](=[O:11])[C:2]2([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]2)[NH:1][C:39]1=[O:40]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 233781-Aminocycloheptanecarboxylic acidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 46142212-Chloro-4-nitrophenyl isocyanate

Product 1

HCID 670603083-(2-Chloro-4-nitrophenyl)-1,3-diazaspiro[4.6]undecane-2,4-dioneYield 18.9%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-aminocycloheptanecarboxylic acid (125 mg, 0.8 mmol) and DMF (0.8 mL) was treated with DBU (0.119 mL, 0.8 mmol) and allowed to stir for 5 min. The solution was then treated with 2-chloro-4-nitrophenylisocyanate (237 mg, 1.2 mmol) in DCE (2 ml) and the resulting mixture was allowed to stir for 30 min at ambient temperature and then reacted in a microwave vessel at 160° C. for 10 min. The reaction mixture was then cooled to rt, diluted with CH2Cl2 and then extracted with water, 1N HCl, sat. aq. NaHCO3, and the solvent removed under reduced pressure. The crude residue was re-crystallized from hot MeOH to afford 51 mg of 3-(2-chloro-4-nitrophenyl)-1,3-diazaspiro[4.6]undecane-2,4-dione, 1.1.15, (18%).

Workup

  1. stirringto stir for 30 min at ambient temperature
  2. customreacted in a microwave vessel at 160° C. for 10 min
  3. extractionextracted with water, 1N HCl, sat. aq. NaHCO3
  4. customthe solvent removed under reduced pressure
  5. customThe crude residue was re-crystallized from hot MeOH

Sources & evidence

ORD record
ord-d4766eb22ee0423d8f4c74bf96350997
Source dataset
uspto-grants-2014_07
Patent number
US08779157B2

Reaction notes

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