Sodium → HCID 13682470, compound

HRID 1415400Notes

Reaction equation

HRID 1415400 reaction equation
[OH:1][CH:2]([CH2:16][O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[CH2:24][C:25]1[S:29][CH:28]=[CH:27][CH:26]=1)[CH2:3][N:4]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:5](=[O:8])[CH2:6]Cl.[Na]>CO>[CH2:9]([N:4]1[C:5](=[O:8])[CH2:6][O:1][CH:2]([CH2:16][O:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[CH2:24][C:25]2[S:29][CH:28]=[CH:27][CH:26]=2)[CH2:3]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 5360545SodiumHCID 13682456HCID 13682456, compound

Product 1

HCID 13682470HCID 13682470, compoundYield 93.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 27 g of N-[2-hydroxy-3-[2-(2-thenyl)phenoxy]propyl]-N-benzyl-chloroacetamide in 100 ml of methanol was added dropwise to a solution of 2.3 g of metallic sodium in 200 ml of methanol with stirring at room temperature. The resulting mixture was stirred under reflux for 3 hours. Then the methanol was distilled off under reduced pressure, and the residue was extracted with 200 ml of benzene. The benzene layer was washed with water and dried over anhydrous magnesium sulfate, and then the benzene was distilled off to give 26 g of crude product as an oil. The oil was purified by column chromatography using a column of silica gel and chloroform as an eluent. The fractions containing the objective product were concentrated to give 23 g of 4-benzyl-2-[2-(2-thenyl)phenoxymethyl]morpholin-5-one as colorless crystals, melting at 97°-99° C.

Workup

  1. stirringThe resulting mixture was stirred
  2. temperatureunder reflux for 3 hours
  3. distillationThen the methanol was distilled off under reduced pressure
  4. extractionthe residue was extracted with 200 ml of benzene
  5. washThe benzene layer was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationthe benzene was distilled off
  8. customto give 26 g of crude product as an oil
  9. customThe oil was purified by column chromatography
  10. additionThe fractions containing the objective product
  11. concentrationwere concentrated

Sources & evidence

ORD record
ord-36cf1ef4a5fb4295ad76bb05af009893
Source dataset
uspto-grants-1977_01
Patent number
US04005084

Reaction notes

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