4-Chlorobenzoyl chloride → HCID 4047648, compound

HRID 439305Notes

Reaction equation

HRID 439305 reaction equation
[OH-:1].[Na+].[NH2:3][CH2:4][CH2:5][O:6][CH:7](O)[CH3:8].[Cl:10][C:11]1[CH:19]=[CH:18][C:14]([C:15](Cl)=[O:16])=[CH:13][CH:12]=1>O>[OH:1][CH2:8][CH2:7][O:6][CH2:5][CH2:4][NH:3][C:15](=[O:16])[C:14]1[CH:18]=[CH:19][C:11]([Cl:10])=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 85014-Chlorobenzoyl chlorideHCID 14798Sodium HydroxideHCID 21989213HCID 21989213, compound

Product 1

HCID 4047648HCID 4047648, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of sodium hydroxide (2.2 g, 0.055 moles) in distilled water (100 ml), aminoethoxyethanol (5.25 g, 0.05 moles) was added and the solution was cooled to 0° C. on an ice bath. Under stirring on the ice bath, p-chloro-benzoylchloride (8.75 g, 0.5 moles) was added thereto drop by drop. The stirring was continued for 3 hours at room temperature and the separated precipitate was filtered off by suction. The mother liquid was extracted with chloroform (3×100 ml). The organic phase was separated, dried with sodium sulfate, filtered and evaporated on a rotary evaporator. The precipitated N-O-di-((4-chloro)-benzoyl)-amino-ethoxyethanol was dissolved in dioxan (50 ml) and sodium hydroxide (22 ml of a 1N solution) was added thereto. The solution was stirred for 2 hours at 40° C., water (50 ml) was added thereto and it was extracted with ethyl acetate (5×50 ml). The organic phase was separated, dried with sodium sulfate, filtered and evaporated on a rotary evaporator. The obtained product was crystallized from diethyl ether.

Workup

  1. additionwas added
  2. filtrationthe separated precipitate was filtered off by suction
  3. extractionThe mother liquid was extracted with chloroform (3×100 ml)
  4. customThe organic phase was separated
  5. dry with materialdried with sodium sulfate
  6. filtrationfiltered
  7. customevaporated on a rotary evaporator
  8. dissolutionThe precipitated N-O-di-((4-chloro)-benzoyl)-amino-ethoxyethanol was dissolved in dioxan (50 ml)
  9. additionsodium hydroxide (22 ml of a 1N solution) was added
  10. additionwater (50 ml) was added
  11. extractionit was extracted with ethyl acetate (5×50 ml)
  12. customThe organic phase was separated
  13. dry with materialdried with sodium sulfate
  14. filtrationfiltered
  15. customevaporated on a rotary evaporator
  16. customThe obtained product was crystallized from diethyl ether

Sources & evidence

ORD record
ord-aa2e2e85facf496d9e0170b9beff40ca
Source dataset
uspto-grants-1996_05
Patent number
US05514654

Reaction notes

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