Acetyl chloride → HCID 59569810, compound

HRID 2071095Notes

Reaction equation

HRID 2071095 reaction equation
CO[CH:3]([O:15]C)[C:4]1[CH:5]=[C:6]([CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1)[NH2:7].C(N(CC)CC)C.[C:24](Cl)(=[O:26])[CH3:25]>ClCCl.CCOCC>[CH:3]([C:4]1[CH:5]=[C:6]([NH:7][C:24](=[O:26])[CH3:25])[CH:8]=[C:9]([C:11]([F:12])([F:13])[F:14])[CH:10]=1)=[O:15]

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 68671840HCID 68671840, compound

Product 1

HCID 59569810HCID 59569810, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To 3-(dimethoxymethyl)-5-(trifluoromethyl)aniline in dichloromethane (5 ml) at 0° C., triethyl amine (0.2 ml) was added followed by acetyl chloride. Reaction mixture was stirred at rt for 2 h. Then dichloromethane was removed under reduced pressure. Reaction mixture was diluted with ether, washed with water, brine and dried. Crude residue was column chromatographed to yield 170 mg of the amide. Then solvent was removed and the crude residue was column purified (40% ethylacetate/60% hexanes) to yield 100 mg of N-(3-(dimethoxymethyl)-5-(trifluoromethyl)phenyl)acetamide.

Workup

  1. customReaction mixture
  2. customThen dichloromethane was removed under reduced pressure
  3. customReaction mixture
  4. washwashed with water, brine
  5. customdried
  6. customchromatographed

Sources & evidence

ORD record
ord-49221635fe3a4647a50ca9edc5686850
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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