Methyl iodide → HCID 23042590, compound

HRID 2165865Notes

Reaction equation

HRID 2165865 reaction equation
[C:1]([C:9]1[CH:21]=[CH:20][C:12]([NH:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[CH:11][CH:10]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:22]([O-])(O)=O.[Na+].CI>CN(C=O)C>[CH3:22][N:13]([CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])[C:12]1[CH:20]=[CH:21][C:9]([C:1](=[O:8])[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 516892Sodium BicarbonateHCID 14072045HCID 14072045, compound

Product 1

HCID 23042590HCID 23042590, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

1.41 g (0.05 mole) of 4-(4-benzoylanilino)butyric acid are dissolved in 15 ml of DMF, and 0.84 g of NaHCO3 (0.01 mole) and 1.42 g (0.01 mole) of methyl iodide are added, and the mixture is stirred at 80° C. for about 3 h. It is then poured onto ice-water, the mixture is extracted with ethyl acetate, the organic phase is dried with MgSO4, and the solvent is evaporated off in vacuo. The residue is chromatographed on silica gel using n-hexane/ethyl acetate as eluent. The oily product is immediately hydrolyzed with 2 N LiOH. The title compound is obtained and has the melting point 111°-113° C.

Workup

  1. additionIt is then poured onto ice-water
  2. extractionthe mixture is extracted with ethyl acetate
  3. dry with materialthe organic phase is dried with MgSO4
  4. customthe solvent is evaporated off in vacuo
  5. customThe residue is chromatographed on silica gel

Sources & evidence

ORD record
ord-b8977ed65a6f4be4b36eadcdb269cf63
Source dataset
uspto-grants-1990_07
Patent number
US04942176

Reaction notes

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