1-Bromo-2-Chloroethane → N-Tertbutoxyacetyl-2-(4-(2-chloroethoxy)-phenyl)-propyl-2-propanesulfonamide

HRID 2120933Notes

Reaction equation

HRID 2120933 reaction equation
[C:1]([O:5][CH2:6][C:7]([NH:9][S:10]([CH:13]([CH3:25])[CH2:14][CH2:15][CH:16]([C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=1)[CH3:17])(=[O:12])=[O:11])=[O:8])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:33][CH2:34][Cl:35]>CC(C)=O>[C:1]([O:5][CH2:6][C:7]([NH:9][S:10]([CH:13]([CH3:25])[CH2:14][CH2:15][CH:16]([C:18]1[CH:19]=[CH:20][C:21]([O:24][CH2:33][CH2:34][Cl:35])=[CH:22][CH:23]=1)[CH3:17])(=[O:12])=[O:11])=[O:8])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 78491-Bromo-2-ChloroethaneHCID 11430Potassium CarbonateHCID 57136326N-tertbutoxyacetyl-2-(4-hydroxyphenyl)propyl-2-propanesulfonamide

Product 1

HCID 57163818N-Tertbutoxyacetyl-2-(4-(2-chloroethoxy)-phenyl)-propyl-2-propanesulfonamideYield 32%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred mixture of N-tertbutoxyacetyl-2-(4-hydroxyphenyl)propyl-2-propanesulfonamide (4.0 g, 11.2 mmol) in acetone (40 mL) was added potassium carbonate (4.64 g, 33.6 mmol) under nitrogen. The resulting mixture was stirred 30 minutes at ambient temperature. Next, 1-bromo-2-chloroethane (1.12 ml, 13.4 mmol) was added and the resulting mixture was heated to reflux while stirring for 48 h. The resulting mixture was cooled and partitioned between ethyl acetate and water. The organic layer was washed with water (2×50 mL) and brine (1×50 mL), dried over magnesium sulfate, and filtered. Evaporation of the filtrate in vacuo followed by chromatography on silica gel eluting with ethyl acetate-hexane gave 1.5 g (32%) of the pure title compound.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux
  3. stirringwhile stirring for 48 h
  4. temperatureThe resulting mixture was cooled
  5. custompartitioned between ethyl acetate and water
  6. washThe organic layer was washed with water (2×50 mL) and brine (1×50 mL)
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customEvaporation of the filtrate in vacuo

Sources & evidence

ORD record
ord-8f086ec0151c4238b032e335c5b6bb75
Source dataset
uspto-grants-2004_02
Patent number
US06693137B1

Reaction notes

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