Iodoethane → HCID 10224080, compound

HRID 1759789Notes

Reaction equation

HRID 1759789 reaction equation
[CH2:1]([N:3]([C:17]1[CH:26]=[CH:25][C:24]2[C:23]([CH3:28])([CH3:27])[CH2:22][CH2:21][C:20]([CH3:30])([CH3:29])[C:19]=2[CH:18]=1)[C:4](=[O:16])[NH:5][C:6]1[CH:15]=[CH:14][C:9]([C:10]([O:12]C)=[O:11])=[CH:8][CH:7]=1)[CH3:2].[H-].[Na+].[CH2:33](I)[CH3:34]>CN(C=O)C>[CH2:33]([N:5]([C:6]1[CH:7]=[CH:8][C:9]([C:10]([OH:12])=[O:11])=[CH:14][CH:15]=1)[C:4]([N:3]([CH2:1][CH3:2])[C:17]1[CH:26]=[CH:25][C:24]2[C:23]([CH3:27])([CH3:28])[CH2:22][CH2:21][C:20]([CH3:30])([CH3:29])[C:19]=2[CH:18]=1)=[O:16])[CH3:34]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 22600034HCID 22600034, compound

Product 1

HCID 10224080HCID 10224080, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

A solution of methyl 4-[3-ethyl-3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ureido]-benzoate (0.25 g, 0.6 mmole) in 15 mL DMF was treated portionwise with 22 mg of sodium hydride (0.92 mmole). After 5 minutes, ethyl iodide (0.062 mL) was added and the reaction mixture was heated to 150° C. for three days. The solvent was removed in vacuo and the residue was diluted in 25 mL ethyl acetate. The organic phase was washed with two 10 mL portions of water and one 10 mL portion of HCl 1N. The organic phase was dried over MgSO4, filtered and concentrated in vacuo. The product was purified by flash chromatography (SiO2, 10% methanol/methylene chloride) giving 90 mg of 4-[1,3-diethyl-3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ureido]-benzoic acid as a pale brown solid. M.P. 169-172° C.

Workup

  1. customThe solvent was removed in vacuo
  2. additionthe residue was diluted in 25 mL ethyl acetate
  3. washThe organic phase was washed with two 10 mL portions of water and one 10 mL portion of HCl 1N
  4. dry with materialThe organic phase was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe product was purified by flash chromatography (SiO2, 10% methanol/methylene chloride)

Sources & evidence

ORD record
ord-d3b40c36f525404cabd872786724d023
Source dataset
uspto-grants-2005_01
Patent number
US06838472B2

Reaction notes

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