1,1'-Carbonyldiimidazole → HCID 66813314, compound

HRID 1891269Notes

Reaction equation

HRID 1891269 reaction equation
[Br:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][NH:7][CH2:8][C:9]([NH:11][CH:12]2[CH2:14][CH2:13]2)=[O:10])=[CH:4][CH:3]=1.[C:17](N1C=CN=C1)(N1C=CN=C1)=[O:18].C(=O)(O)[O-].[Na+]>C(#N)C.CN(C)C1C=CN=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[CH2:8][C:9](=[O:10])[N:11]([CH:12]3[CH2:13][CH2:14]3)[C:17]2=[O:18])=[CH:15][CH:16]=1

Participants

6

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 516892Sodium BicarbonateHCID 43401847HCID 43401847, compound

Product 1

HCID 66813314HCID 66813314, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2-(4-bromobenzylamino)-N-cyclopropylacetamide (7H4) (28.3 mmol, 8.0 g) in acetonitrile (200 ml) was added carbonyldiimidazole (56.5 mmol, 9.16 g) and 4-dimethylaminopyridine (56.5 mmol, 6.90 g). The reaction mixture was heated to 60° C. and stirred overnight before cooling to room temperature. Saturated sodium bicarbonate solution was added and the mixture extracted with EtOAc (×3). The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated and the residue purified on silica eluting with heptane/acetone 9:1 to 7:3 to give 1-(4-bromobenzyl)-3-cyclopropylimidazolidine-2,4-dione (7H5) 8.3 g (98%); 1H NMR (400 MHz, CDCl3) δ 7.50 (d, 2H) 7.13 (d, 2H) 4.50 (s, 2H) 3.66 (s, 2H) 2.62 (m, 1H) 0.97 (d, 4H).

Workup

  1. temperaturebefore cooling to room temperature
  2. extractionthe mixture extracted with EtOAc (×3)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customthe residue purified on silica eluting with heptane/acetone 9:1 to 7:3

Sources & evidence

ORD record
ord-98400514268b4f7c99803e7ba30e9c19
Source dataset
uspto-grants-2013_08
Patent number
US08507521B2

Reaction notes

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