Water → HCID 90281980, compound

HRID 1497536Notes

Reaction equation

HRID 1497536 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([O:10][CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[CH:7]=[CH:6][C:3]=1[NH:4][CH3:5].[Cl:19][CH2:20][C:21](Cl)=[O:22].C(N(CC)CC)C.O>ClCCl>[Cl:19][CH2:20][C:21]([N:4]([C:3]1[CH:6]=[CH:7][C:8]([O:10][CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])=[CH:9][C:2]=1[Cl:1])[CH3:5])=[O:22]

Participants

6

Reactant 4

HCID 962WaterHCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 90281997HCID 90281997, compound

Product 1

HCID 90281980HCID 90281980, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-chloro-N-methyl-4-{[2-(trimethylsilyl)ethoxy]methoxy}aniline (1.00 g) in dichloromethane (20.0 mL) were added chloroacetyl chloride (0.415 mL) and triethylamine (0.872 mL) under ice-cooling, followed by stirring for 1 hour under ice-cooling. To the reaction mixture was added water, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, then dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain 2-chloro-N-(2-chloro-4-{[2-(trimethylsilyl)ethoxy]methoxy}phenyl)-N-methylacetamide (1.08 g).

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-df8537c4df914057ac6323586fcb601e
Source dataset
uspto-grants-2015_12
Patent number
US09199927B2

Reaction notes

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