Hydrochloric Acid → HCID 53770272, compound

HRID 1598907Notes

Reaction equation

HRID 1598907 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:22])[CH2:10][NH:11][C:12]([NH:14][C:15]1[CH:16]=[C:17]([CH3:21])[CH:18]=[CH:19][CH:20]=1)=[O:13].[I-].[K+].[C:25]([O:29][C:30](=[O:33])[CH2:31]Br)([CH3:28])([CH3:27])[CH3:26].C(=O)([O-])[O-].[K+].[K+].Cl>CS(C)=O.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C.O>[I:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]([CH2:31][C:30]([O:29][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:33])[C:9](=[O:22])[CH2:10][NH:11][C:12]([NH:14][C:15]1[CH:16]=[C:17]([CH3:21])[CH:18]=[CH:19][CH:20]=1)=[O:13]

Participants

10

Reactant 5

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 18930549HCID 18930549, compound

Product 1

HCID 53770272HCID 53770272, compoundYield 92%

Reagents, catalysts & solvents 4

HCID 74236Tetrabutylammonium BromideCatalystHCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-(2-iodophenyl)-2-(3-m-tolylureido)acetamide (1.02 g, 2.5 mmol) in DMSO (5 ml) are added at room temperature potassium iodide (83 mg, 0.2 mmol), tetra-n-butylammonium bromide (81 mg, 0.1 mmol), t-butylbromoacetate (0.55 ml, 3.75 mmol) and potassium carbonate (1.04 g, 7.5 mmol), and stirred at room temperature for 2.25 hours. To the reaction mixture are added water and ethyl acetate, and the pH is adjusted to 2 with 2N hydrochloric acid. The aqueous layer is extracted twice with ethyl acetate. The organic layer is washed with 0.1N hydrochloric acid, water and saturated saline, dried over anhydrous magnesium sulfate, and then concentrated. To the residue is added isopropylether, and the precipitated solid is filtered off to obtain the objective compound (1.20 g). Yield 92%.

Workup

  1. extractionThe aqueous layer is extracted twice with ethyl acetate
  2. washThe organic layer is washed with 0.1N hydrochloric acid, water and saturated saline
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. additionTo the residue is added isopropylether
  6. filtrationthe precipitated solid is filtered off

Sources & evidence

ORD record
ord-7bda12a7c0fc4d3d93900e4523bc204e
Source dataset
uspto-grants-1998_04
Patent number
US05739162

Reaction notes

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