1,1'-Carbonyldiimidazole → HCID 59540652, compound

HRID 1677542Notes

Reaction equation

HRID 1677542 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH2:12])[CH:5]=[C:6]([O:8][CH2:9][O:10][CH3:11])[CH:7]=1.[CH3:13][C:14]1([CH3:21])[CH2:19][C:18](=O)[O:17][C:15]1=[O:16].C(N1C=CN=C1)(N1C=CN=C1)=O>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([N:12]2[C:18](=[O:17])[CH2:19][C:14]([CH3:21])([CH3:13])[C:15]2=[O:16])[CH:5]=[C:6]([O:8][CH2:9][O:10][CH3:11])[CH:7]=1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 870672,2-Dimethylsuccinic anhydrideHCID 59540873HCID 59540873, compound

Product 1

HCID 59540652HCID 59540652, compoundYield 2,352.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 3-bromo-5-methoxymethoxy-phenylamine (1.0 g, 4.31 mmol) in methylene chloride (25 ml) was added 2,2-dimethylsuccinic anhydride (580 mg, 0.195 mmol). The mixture was heated to 50° C. (oil bath) for 1 hour and then stirred over night at ambient at which point a large amount of precipitate had formed. Carbonyldiimidazole (839 mg, 5.17 mmol) was added and within 2 minutes a homogeneous solution was obtained. The material was stirred over night and then the crude was adsorbed onto silica gel (12 g). Purification by silica gel chromatography eluting with 6%-45% EtOAc in hexanes afforded 1.57 g of 1-(3-bromo-5-methoxymethoxy-phenyl)-3,3-dimethyl-pyrrolidine-2,5-dione as a viscous yellow-white oil.

Workup

  1. customhad formed
  2. customwas obtained
  3. stirringThe material was stirred over night
  4. customPurification by silica gel chromatography
  5. washeluting with 6%-45% EtOAc in hexanes

Sources & evidence

ORD record
ord-b86daa3bb588409cb73adb0c2eb6319b
Source dataset
uspto-grants-2011_08
Patent number
US08008298B2

Reaction notes

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