Diethyl Ether → Benzyl 3-benzyl-2,2-dimethyl-4-oxoimidazolidine-1-carboxylate

HRID 1675184Notes

Reaction equation

HRID 1675184 reaction equation
[CH2:1]([N:8]1[C:12](=[O:13])[CH2:11][NH:10][C:9]1([CH3:15])[CH3:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:16]([O:23][C:24](Cl)=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.OS([O-])(=O)=O.[K+].CCOCC>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH2:1]([N:8]1[C:12](=[O:13])[CH2:11][N:10]([C:24]([O:23][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:25])[C:9]1([CH3:15])[CH3:14])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 10387Benzyl chloroformate2×HCID 516920Potassium bisulfateHCID 574330893-Benzyl-2,2-dimethylimidazolidin-4-one

Product 1

HCID 57433090Benzyl 3-benzyl-2,2-dimethyl-4-oxoimidazolidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A cold (0° C.) solution of 3-benzyl-2,2-dimethylimidazolidin-4 -one (2.28 g, 11.16 mmol) in CH2Cl2 (25 mL) was treated with benzylchloroformate (0.96 mL, 6.70 mmol), a solution of 4-dimethylaminopyridine (1.71 g, 13.95 mmol) in CH2Cl2 (10 mL), and again with benzylchloroformate (0.96 mL, 6.70 mmol). The solution was stirred for 30 min and poured into aqueous 10% KHSO4 solution. The layers were separated, and the organic was washed twice with water and once with brine. The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo to afford an orange oil. The oil was treated with Et2O causing a precipitate which was filtered to afford the product as a white solid. 1H NMR (400 MHz, CDCl3) δ 7.37 (m, 10H), 5.14 (s, 2H), 4.54 (s, 2H), 4.11 (s, 6H), 1.56 (s, 6H); ES MS (M+1)=339.

Workup

  1. customThe layers were separated
  2. washthe organic was washed twice with water and once with brine
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto afford an orange oil
  7. filtrationwas filtered

Sources & evidence

ORD record
ord-e45e0781e6024429be02e05fe2ff6c85
Source dataset
uspto-grants-2011_08
Patent number
US08003653B2

Reaction notes

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