Acetyl chloride → HCID 22119058, compound

HRID 1275072Notes

Reaction equation

HRID 1275072 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 step (f) above] 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-8cbf8e5c6ab74d4fa258ca6c7a43ed95
Source dataset
uspto-grants-2000_12
Patent number
US06159997

Reaction notes

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