Acetic Anhydride → HCID 18671324, compound

HRID 1596150Notes

Reaction equation

HRID 1596150 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 miL). 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 miL)
  6. dry with materialThe organic layer is dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-a152fb6be5b64367ae56ba7df431aa90
Source dataset
uspto-grants-2001_09
Patent number
US06291413B1

Reaction notes

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