Chloroacetyl chloride → N-[4-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-2-chloro-acetamide

HRID 1419924Notes

Reaction equation

HRID 1419924 reaction equation
[C:1]([Si:5]([CH3:15])([CH3:14])[O:6][C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[Na+].[Na+].[Cl:22][CH2:23][C:24](Cl)=[O:25]>CC(C)=O>[C:1]([Si:5]([CH3:15])([CH3:14])[O:6][C:7]1[CH:8]=[CH:9][C:10]([NH:13][C:24](=[O:25])[CH2:23][Cl:22])=[CH:11][CH:12]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 10340Sodium CarbonateHCID 117155534-((Tert-butyldimethylsilyl)oxy)aniline

Product 1

HCID 70046914N-[4-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-2-chloro-acetamideYield 85%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

4-(tert-Butyl-dimethyl-silanyloxy)-phenylamine (2.23 g, 10 mmol) was dissolved in acetone (25 ml). After addition of Na2CO3 (3.2 g, 30 mmol), chloroacetylchloride (0.96 ml, 12 mmol) was added dropwise. After 1 hour at room temperature, the reaction mixture was quenched with H2O (100 ml) and the aqueous phase was extracted with CH2Cl2 (3×10 ml). Combined organic phases were dried over Na2SO4 and concentrated. The residue was chromatographed over silica gel (hexane-ethyl acetate 9:1 then hexane-ethyl acetate 4:1) to provide N-[4-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-2-chloro-acetamide (2.55 g, 71%) as a colorless solid, m.p. 107°-108° C. and MS: m/e=299 (M+).

Workup

  1. additionwas added dropwise
  2. customthe reaction mixture was quenched with H2O (100 ml)
  3. extractionthe aqueous phase was extracted with CH2Cl2 (3×10 ml)
  4. dry with materialCombined organic phases were dried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was chromatographed over silica gel (hexane-ethyl acetate 9:1

Sources & evidence

ORD record
ord-0046db0f61c143e0a0658104360367d9
Source dataset
uspto-grants-1999_03
Patent number
US05889026

Reaction notes

Loading…