Water → Ethyl 6-(4-acetylamino-2,6-dichlorophenoxy)hexanoate

HRID 1634249Notes

Reaction equation

HRID 1634249 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8].C(=O)([O-])[O-].[Cs+].[Cs+].[Cl:18][C:19]1[CH:20]=[C:21]([NH:27][C:28](=[O:30])[CH3:29])[CH:22]=[C:23]([Cl:26])[C:24]=1[OH:25].O>CC(C)=O>[C:28]([NH:27][C:21]1[CH:22]=[C:23]([Cl:26])[C:24]([O:25][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])=[C:19]([Cl:18])[CH:20]=1)(=[O:30])[CH3:29]

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 117544Ethyl 6-bromohexanoateHCID 100821803',5'-Dichloro-4'-hydroxyacetanilide

Product 1

HCID 18677764Ethyl 6-(4-acetylamino-2,6-dichlorophenoxy)hexanoate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

13.3 ml (74.9mmol) of ethyl 6-bromohexanoate and 52.1 g (160 mmol) of cesium carbonate were added to a solution of 15.0 g (68.1 mmol) of N-(3,5-dichloro-4-hydroxyphenyl)acetamide in 300 ml of acetone. The suspension was boiled under reflux for 8 hours, and then 600 ml of water were added. The mixture was extracted twice with 400 ml of dichloromethane and with 400 ml of MTB ether each time. The combined organic phases were washed with water and concentrated in a rotary evaporator. The product was employed in the next step without purification. Crude yield was 30 g.

Workup

  1. temperatureunder reflux for 8 hours
  2. extractionThe mixture was extracted twice with 400 ml of dichloromethane and with 400 ml of MTB ether each time
  3. washThe combined organic phases were washed with water
  4. concentrationconcentrated in a rotary evaporator
  5. customThe product was employed in the next step without purification

Sources & evidence

ORD record
ord-1f704998465f455ebffc5809c9a41686
Source dataset
uspto-grants-2003_01
Patent number
US06506778B2

Reaction notes

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