1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 18509764, compound

HRID 1370114Notes

Reaction equation

HRID 1370114 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([N+:14]([O-:16])=[O:15])[CH:5]=[CH:6][C:7]=1[NH:8][CH:9]1[CH2:13][CH2:12][CH2:11][CH2:10]1.N12CCCN=C1CCCCC2.Cl[C:29](Cl)([O:31]C(=O)OC(Cl)(Cl)Cl)Cl>ClCCCl.C(Cl)(Cl)Cl>[CH:9]1([N:8]2[C:7]3[CH:6]=[CH:5][C:4]([N+:14]([O-:16])=[O:15])=[CH:3][C:2]=3[NH:1][C:29]2=[O:31])[CH2:10][CH2:11][CH2:12][CH2:13]1

Participants

6

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 94429TriphosgeneHCID 18509727HCID 18509727, compound

Product 1

HCID 18509764HCID 18509764, compoundYield 83.7%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6212ChloroformSolvent

Procedure

To a solution of 3-amino-4-cyclopentylamino-1-nitrobenzene (445 mg) and 1,8-diazabicyclo[5.4.0]undec-7-ene (0.6 mL) in 1,2-dichloroethane (5 mL) was added triphosgene (358 mg) at 0° C., and the mixture was stirred at room temperature under nitrogen atmosphere for 20 minutes. The resulting mixture was diluted with chloroform and washed successively with water(twice) and brine. The organic layer was dried over magnesium sulfate and evaporated in vacuo. The residue was subjected to a silica gel column chromatography eluting with a mixture of n-hexane and ethyl acetate (3:1). The obtained substance was triturated with diisopropyl ether to give 1-cyclopentyl-5-nitro-2,3-dihydro-1H-benzimidazol-2-one (249.8 mg) as an off-white solid.

Workup

  1. washwashed successively with water(twice) and brine
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. customevaporated in vacuo
  4. washeluting with a mixture of n-hexane and ethyl acetate (3:1)
  5. customThe obtained substance was triturated with diisopropyl ether

Sources & evidence

ORD record
ord-b5105ce457294ea185cdcfc31094b8f1
Source dataset
uspto-grants-2003_06
Patent number
US06582351B1

Reaction notes

Loading…