Imidazole → HCID 66687296, compound

HRID 2409500Notes

Reaction equation

HRID 2409500 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:7](=[O:14])[NH:6][C:5]2=[O:15].N1C=CN=C1.[CH3:21][N:22]([CH3:26])[CH2:23][CH2:24]N.CCOCC>C1C=CC(C2C=CC=CC=2)=CC=1.C1C=CC(OC2C=CC=CC=2)=CC=1>[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:7](=[O:14])[N:6]([CH2:24][CH2:23][N:22]([CH3:26])[CH3:21])[C:5]2=[O:15]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 3283Diethyl EtherHCID 66053N,N-DimethylethylenediamineHCID 151445685-Amino-6-nitro-1H-isoindole-1,3(2H)-dione

Product 1

HCID 66687296HCID 66687296, compoundYield 95.2%

Reagents, catalysts & solvents 1

HCID 246701,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene)Solvent

Conditions

Temperature
150 °C

Procedure

To a suspension of 5-Amino-6-nitroisoindoline-1,3-dione (5.0 g, 24.15 mmol) in Dowtherm (75 mL) were added imidazole (1.64 g, 24.15 mmol) and N1,N1-dimethylethane-1,2-diamine (3.16 mL, 24.15 mmol) and the resulting mixture was heated at 150° C. for overnight. The reaction mixture was cooled to RT, was added ether (100 mL). The yellow precipitate was collected by filtration and washed with ether (2×50 mL) and dried to afford 5-Amino-2-(2-(dimethylamino)ethyl)-6-nitroisoindoline-1,3-dione (6.4 g, 95%) as a yellow solid.

Workup

  1. temperatureThe reaction mixture was cooled to RT
  2. filtrationThe yellow precipitate was collected by filtration
  3. washwashed with ether (2×50 mL)
  4. customdried

Sources & evidence

ORD record
ord-d9420187883f4c198ea76f0e4d133243
Source dataset
uspto-grants-2014_08
Patent number
US08815906B2

Reaction notes

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