Acetonitrile → [2-Chloro-6-(trimethylsilyl)benzoyl]ethylcarbamic acid, 1,1-dimethylethyl ester

HRID 610954Notes

Reaction equation

HRID 610954 reaction equation
[Cl:1][C:2]1[CH:12]=[CH:11][CH:10]=[C:9]([Si:13]([CH3:16])([CH3:15])[CH3:14])[C:3]=1[C:4](NCC)=[O:5].[C:17](=[O:28])([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])OC(C)(C)C.[C:29](#[N:31])[CH3:30]>CN(C)C1C=CN=CC=1>[Cl:1][C:2]1[CH:12]=[CH:11][CH:10]=[C:9]([Si:13]([CH3:14])([CH3:15])[CH3:16])[C:3]=1[C:4]([CH2:30][CH2:29][NH:31][C:17](=[O:28])[O:23][C:24]([CH3:25])([CH3:26])[CH3:27])=[O:5]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) ester3×HCID 186303792-Chloro-n-ethyl-6-(trimethylsilyl)benzamide

Product 1

HCID 57096133[2-Chloro-6-(trimethylsilyl)benzoyl]ethylcarbamic acid, 1,1-dimethylethyl ester

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

To a solution of the compound of example 45 (3.83 g, 15 mmol) and di-t-butyl carbonate (3.60 g, 16.5 mmol) in acetonitrile was added 4-dimethylaminopyridine (0.18 g, 1.5 mmol). The solution was stirred at RT for 1 day, additional di-t-butyl carbonate (3.60 g) was added and stirring was continued for 3 days. Additional di-t-butyl carbonate (3.60 g) was added and the reaction was stirred overnight and concentrated. The residue was diluted with ether, washed with sat citric acid, sat NaHCO3, brine, dried (MgSO4) and concentrated to afford the title compound. The crude product was purified by flash chromatography (ethyl acetate/hexanes) and recrystallization from hexanes (-78° C.) to afford the title compound as a white solid (2.65 g, 50%). m.p. 51-52° C.

Workup

  1. stirringstirring
  2. waitwas continued for 3 days
  3. stirringthe reaction was stirred overnight
  4. concentrationconcentrated
  5. additionThe residue was diluted with ether
  6. washwashed
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-82d7321abbcc4bd5bbc6def4be196b71
Source dataset
uspto-grants-1999_12
Patent number
US05998466

Reaction notes

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