Ethanolamine → HCID 21409990, compound

HRID 328502Notes

Reaction equation

HRID 328502 reaction equation
[C:1]([O:4][CH2:5][CH2:6][N:7]([C:12]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:13]=1[C:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[F:22])=[O:15])[C:8](=[O:11])[CH2:9]Br)(=[O:3])[CH3:2].[CH2:28]([N:30](CC)CC)[CH3:29].C(CN)O>C1C=CC=CC=1>[C:1]([O:4][CH2:5][CH2:6][N:7]1[C:12]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:13]=2[C:14]2([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[F:22])[O:15][CH2:29][CH2:28][N:30]2[CH2:9][C:8]1=[O:11])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 700EthanolamineHCID 8471TriethylamineHCID 21409981HCID 21409981, compound

Product 1

HCID 21409990HCID 21409990, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution containing 1.5g (0.0033 M) of 2-[N-(2-acetoxyethyl)-N-(2-bromoacetyl)amino]-5-chloro-2'-fluorobenzophenone, 0.5 ml of triethylamine and 0.23g (0.0036 M) of ethanolamine in 15 ml of benzene was kept at room temperature for 65 hours and then was partitioned between 25 ml of ethyl acetate and 25 ml of water. The organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate and evaporated to dryness. The residue was partioned between 20 ml of ether and 20 ml of 1N hydrochloric acid. The acid layer was separated and extracted with 25 ml of ethyl acetate. The organic layer was then washed with 20 ml of dilute ammonium hydroxide, dried over anhydrous sodium sulfate and evaporated to dryness. The residual oil was crystallized from ether and recrystallized from a mixture of methanol and water to give the above named product as white prisms, m.p. 120°-123°.

Workup

  1. customwas partitioned between 25 ml of ethyl acetate and 25 ml of water
  2. customThe organic layer was separated
  3. washwashed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated to dryness
  6. customThe acid layer was separated
  7. extractionextracted with 25 ml of ethyl acetate
  8. washThe organic layer was then washed with 20 ml of dilute ammonium hydroxide
  9. dry with materialdried over anhydrous sodium sulfate
  10. customevaporated to dryness
  11. customThe residual oil was crystallized from ether
  12. customrecrystallized from a mixture of methanol and water
  13. customto give the above named product as white prisms, m.p. 120°-123°

Sources & evidence

ORD record
ord-66479c6cc2fd4edba80ba7e0c6dd406a
Source dataset
uspto-grants-1977_04
Patent number
US04017532

Reaction notes

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