Acetyl chloride → HCID 14673827, compound

HRID 1494436Notes

Reaction equation

HRID 1494436 reaction equation
[OH:1][N:2]([CH:4]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH:13]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[CH3:14])=[CH:8][CH:7]=1)[CH3:5])[OH:3].[C:22](Cl)(=[O:24])[CH3:23].C([N:28]([CH2:31]C)CC)C>C1COCC1>[OH:3][N:2]([CH:4]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH:13]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[CH3:14])=[CH:8][CH:7]=1)[CH3:5])[C:22](=[O:24])[CH3:23].[OH:1][N:2]([CH:4]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH:13]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[CH3:14])=[CH:8][CH:7]=1)[CH3:5])[C:31]([NH2:28])=[O:24]

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 19828167HCID 19828167, compound

Product 2

HCID 14673827HCID 14673827, compoundHCID 14673828HCID 14673828, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-Hydroxy-N-(1-(4-(1-(4-fluorophenyl)ethoxy)-phenyl)ethyl]acetamide was prepared by the reaction of the hydroxylamine compound prepared in step (d) above with two equivalents of acetyl chloride in the presence of triethylamine in THF. The intermediate N,O-diacetyl compound was extracted with ethyl acetate, dried over anhydrous magnesium sulfate, after which the solvent was evaporated. The residue was taken up in isopropyl alcohol and a solution of lithium hydroxide in water was added. The mixture was stirred until the reaction was complete, and then neutralized by the addition of 2N HCl. This mixture was extracted with ether, the ether solution dried over anhydrous magnesium sulfate, and evaporated to yield the title compound.

Workup

  1. extractionThe intermediate N,O-diacetyl compound was extracted with ethyl acetate
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customafter which the solvent was evaporated
  4. additiona solution of lithium hydroxide in water was added
  5. additionneutralized by the addition of 2N HCl
  6. extractionThis mixture was extracted with ether
  7. dry with materialthe ether solution dried over anhydrous magnesium sulfate
  8. customevaporated

Sources & evidence

ORD record
ord-0b1e70dfe9124df895d08eb58cf10cc4
Source dataset
uspto-grants-1991_06
Patent number
US05026729

Reaction notes

Loading…