Water → HCID 14555681, compound

HRID 1723417Notes

Reaction equation

HRID 1723417 reaction equation
Cl.[NH2:2][OH:3].C(=O)([O-])[O-].[Na+].[Na+].[CH2:10]([O:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31](Cl)=[O:32])=[CH:19][CH:18]=1)[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15].O>C(Cl)Cl>[CH2:10]([O:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31]([NH:2][OH:3])=[O:32])=[CH:19][CH:18]=1)[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15]

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 14555679HCID 14555679, compound

Product 1

HCID 14555681HCID 14555681, compoundYield 10.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a cold, stirring suspension of 1.2 gms hydroxylamine hydrochloride and 1.7 gms sodium carbonate in 40 ml CH2Cl2 was added dropwise 4.2 gms 9(4-hexyloxyphenyl)nonanoyl chloride. The mixture was stirred for 1/2 hr in the cold, then 2 ml water was added, and the reaction was stirred at room temperature overnight. The suspension was then diluted with CH2Cl2, washed three times with water and once with NaCl solution, then dried over MgSO4. The drying agent was filtered off and the solvent was removed in vacuo to give a solid which was crystallized from CHCl3 :hexanes and then hexanes. Impurities were still present by thin layer chromatography, so the solid was dissolved in 3:1 benzene:hexanes, shaken with 150 gms silica gel, and the silica gel washed with ethyl acetate. The solid remaining on evaporation of the solvent was purified by column chromatography on silica gel with 30% ethyl acetate:CHCl3. The main fraction had Rf=0.4 by thin layer chromatography. The residue from the collected fractions was crystallized twice from CH2Cl2 to give 0.45 gms product of m.p. 94°-6°.

Workup

  1. additionwas added
  2. stirringthe reaction was stirred at room temperature overnight
  3. washwashed three times with water
  4. dry with materialonce with NaCl solution, then dried over MgSO4
  5. filtrationThe drying agent was filtered off
  6. customthe solvent was removed in vacuo
  7. customto give a solid which
  8. customwas crystallized from CHCl3
  9. dissolutionso the solid was dissolved in 3:1 benzene
  10. stirringhexanes, shaken with 150 gms silica gel
  11. washthe silica gel washed with ethyl acetate
  12. customThe solid remaining on evaporation of the solvent
  13. customwas purified by column chromatography on silica gel with 30% ethyl acetate
  14. customThe residue from the collected fractions was crystallized twice from CH2Cl2

Sources & evidence

ORD record
ord-1b4c1dc23b5d4779966fbd400c4c14f8
Source dataset
uspto-grants-1989_08
Patent number
US04861798

Reaction notes

Loading…