Sodium Hydroxide → HCID 58758914, compound

HRID 2242524Notes

Reaction equation

HRID 2242524 reaction equation
[Cl:1][C:2]([Cl:27])=[CH:3][CH2:4][O:5][C:6]1[CH:11]=[C:10]([Cl:12])[C:9]([N:13]2[CH2:18][CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15][CH2:14]2)=[C:8]([Cl:26])[CH:7]=1.[Cl-].[Al+3].[Cl-].[Cl-].[OH-].[Na+]>C(Cl)Cl>[Cl:27][C:2]([Cl:1])=[CH:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([Cl:26])[C:9]([N:13]2[CH2:14][CH2:15][NH:16][CH2:17][CH2:18]2)=[C:10]([Cl:12])[CH:11]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 6451240Aluminum(III) ChlorideHCID 46178406HCID 46178406, compound

Product 1

HCID 58758914HCID 58758914, compoundYield 86.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under a nitrogen atmosphere, a stirred solution of 1.8 gram (0.0039 mole) of tert-butyl 4-[4-(3,3-dichloroprop-2-enyloxy)-2,6-dichlorophenyl]piperazinecarboxylate in 30 mL of methylene chloride was cooled to about 0° C. and 0.53 gram (0.0039 mole) of aluminum chloride was added portion-wise. Upon completion of addition the reaction mixture was allowed to warm to ambient temperature where it stirred during a five hour period. After this time 20 mL of an aqueous solution of 10% sodium hydroxide was added dropwise, then the mixture was extracted with two 25 mL portions of ethyl acetate. The combined extracts were washed with one 25 mL portion of an aqueous solution saturated with sodium chloride, dried with sodium sulfate and filtered. The filtrate was concentrated under reduced pressure, yielding 1.2 grams of the subject compound. The NMR spectrum was consistent with the proposed structure.

Workup

  1. additionUpon completion of addition the reaction mixture
  2. extractionthe mixture was extracted with two 25 mL portions of ethyl acetate
  3. washThe combined extracts were washed with one 25 mL portion of an aqueous solution saturated with sodium chloride
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-38ad078611774b589bf5dfb1e9f23f28
Source dataset
uspto-grants-2010_03
Patent number
US07671201B2

Reaction notes

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