Water → HCID 14157298, compound

HRID 354905Notes

Reaction equation

HRID 354905 reaction equation
[H-].[Na+].[CH2:3]([O:5][CH2:6][C:7]([NH:9][C:10]1[C:15]([CH3:16])=[CH:14][CH:13]=[C:12]([N+:17]([O-:19])=[O:18])[C:11]=1[CH3:20])=[O:8])[CH3:4].Br[CH:22]([CH3:27])[C:23]([O:25][CH3:26])=[O:24].O>O1CCCC1>[CH3:26][O:25][C:23]([CH:22]([N:9]([C:7](=[O:8])[CH2:6][O:5][CH2:3][CH3:4])[C:10]1[C:15]([CH3:16])=[CH:14][CH:13]=[C:12]([N+:17]([O-:19])=[O:18])[C:11]=1[CH3:20])[CH3:27])=[O:24]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 95576Methyl 2-bromopropionateHCID 14157297HCID 14157297, compound

Product 1

HCID 14157298HCID 14157298, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
55 °C

Procedure

To a solution of 3 g of 55% sodium hydride in 70 ml of anhydrous tetrahydrofuran saturated with nitrogen is added dropwise, at room temperature, with stirring and while simultaneously introducing nitrogen, a solution of 16 g N-ethoxyacetyl-2,6-dimethyl-3-nitroaniline in 30 ml of the same solvent. After the weakly exothermic reaction has subsided, the mixture is heated to 55° C. and 12.7 g of methyl 2-bromopropionate in 20 ml of tetrahydrofurane are added. During this addition the temperature rises to 60° C. The mixture is stirred for 12 hours at 55° C., then cooled to room temperature, poured into 100 ml of water and extracted with two 100 ml portions of ethyl acetate. The combined extracts are washed with water, dried over sodium sulfate, and excess solvent is removed in vacuo. The oily crude product is purified by column chromatography over silica gel, using a 1:1 mixture of chloroform/diethyl ether as eluant. Fractions 5 to 30 are combined and the eluant is removed in vacuo. Compound 31 is a viscous oil with a refractive index of nD24 =1.5325.

Workup

  1. customAfter the weakly exothermic reaction
  2. additionDuring this addition the temperature
  3. customrises to 60° C
  4. stirringThe mixture is stirred for 12 hours at 55° C.
  5. temperaturecooled to room temperature
  6. extractionextracted with two 100 ml portions of ethyl acetate
  7. washThe combined extracts are washed with water
  8. dry with materialdried over sodium sulfate, and excess solvent
  9. customis removed in vacuo
  10. customThe oily crude product is purified by column chromatography over silica gel
  11. additiona 1:1 mixture of chloroform/diethyl ether as eluant
  12. customthe eluant is removed in vacuo

Sources & evidence

ORD record
ord-c19dce10b0f04f288bfa016d423da51b
Source dataset
uspto-grants-1983_03
Patent number
US04377587

Reaction notes

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