Acetyl chloride → HCID 22119058, compound

HRID 1419113Notes

Reaction equation

HRID 1419113 reaction equation
C(N(CC)CC)C.[C:8](Cl)(=[O:10])[CH3:9].[C:12]([O:16][C:17]([N:19]([CH3:30])[C:20]1[CH:25]=[C:24]([CH3:26])[C:23]([OH:27])=[C:22]([CH3:28])[C:21]=1[CH3:29])=[O:18])([CH3:15])([CH3:14])[CH3:13]>O1CCCC1.O>[C:12]([O:16][C:17]([N:19]([CH3:30])[C:20]1[CH:25]=[C:24]([CH3:26])[C:23]([O:27][C:8](=[O:10])[CH3:9])=[C:22]([CH3:28])[C:21]=1[CH3:29])=[O:18])([CH3:15])([CH3:14])[CH3:13]

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 22119052HCID 22119052, compound

Product 1

HCID 22119058HCID 22119058, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

5.64 ml of dehydrated triethylamine and 2.9 ml of acetyl chloride were added at room temperature to a solution of 7.2 g of N-t-butoxycarbonyl-N-methyl-4-hydroxy-2,3,5-trimethylaniline (prepared as described in Preparation 15) in 100 ml of dehydrated tetrahydrofuran, and the resulting mixture was stirred for 1 hour, after which it was allowed to stand overnight. The reaction mixture was then diluted with water and the aqueous mixture was extracted with ethyl acetate. The extract was washed with water and with a saturated aqueous solution of sodium chloride, in that order, after which it was dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure, after which the residue was triturated with ice-cooled hexane to cause crystallization. The crystals were collected by filtration and washed with ice-cooled hexane to give 6.25 g of the title compound, melting at 103°-104° C.

Workup

  1. waitto stand overnight
  2. extractionthe aqueous mixture was extracted with ethyl acetate
  3. washThe extract was washed with water and with a saturated aqueous solution of sodium chloride, in that order
  4. dry with materialafter which it was dried over anhydrous magnesium sulfate
  5. customThe solvent was removed by distillation under reduced pressure
  6. customafter which the residue was triturated with ice-
  7. temperaturecooled hexane
  8. customcrystallization
  9. filtrationThe crystals were collected by filtration
  10. washwashed with ice-
  11. temperaturecooled hexane

Sources & evidence

ORD record
ord-60cb366da1304f7d95ee82a36f0765f2
Source dataset
uspto-grants-1999_03
Patent number
US05886014

Reaction notes

Loading…