Acetic Anhydride → HCID 18671324, compound

HRID 2230010Notes

Reaction equation

HRID 2230010 reaction equation
C(N(CC)CC)C.[CH3:8][O:9][NH:10][C:11](=[O:20])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].[C:21](OC(=O)C)(=[O:23])[CH3:22]>C(Cl)Cl>[CH3:8][O:9][N:10]([C:11](=[O:20])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[C:21](=[O:23])[CH3:22]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 18671325HCID 18671325, compound

Product 1

HCID 18671324HCID 18671324, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A 100 mL round-bottom flask equipped with a magnetic stir bar, argon inlet and pressure equalizing addition funnel is charged with methylene chloride (22.5 mL), triethylamine (3.80 g, 2 eq) and N-methoxynonanamide (3.5 g, 1 eq). The reaction mixture is stirred and cooled in an ice bath. Acetic anhydride (2.88 g, 1.5 eq) is then added dropwise. The reaction slowly warms to room temperature overnight. The reaction mixture is diluted with methylene chloride (50 mL) and washed with 0.05 M hydrochloric acid solution (1×50 mL), saturated aqueous sodium bicarbonate solution (3×50 mL) and brine (1×50 mL). The organic layer is dried over sodium sulfate, filtered and concentrated under vacuum.

Workup

  1. customA 100 mL round-bottom flask equipped with a magnetic stir bar, argon inlet
  2. additionaddition funnel
  3. temperaturecooled in an ice bath
  4. customThe reaction
  5. washwashed with 0.05 M hydrochloric acid solution (1×50 mL), saturated aqueous sodium bicarbonate solution (3×50 mL) and brine (1×50 mL)
  6. dry with materialThe organic layer is dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-6f890b4edbc44756aff7d548756d8db5
Source dataset
uspto-grants-2002_07
Patent number
US06423676B1

Reaction notes

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