Hydrochloric Acid → 3-[4-(3,3-Dichloroprop-2-enyloxy)-2,6-dichlorophenoxy]propylamine hydrochloride

HRID 1611462Notes

Reaction equation

HRID 1611462 reaction equation
[Cl:1][C:2]([Cl:26])=[CH:3][CH2:4][O:5][C:6]1[CH:23]=[C:22]([Cl:24])[C:9]([O:10][CH2:11][CH2:12][CH2:13][NH:14]C(OC(C)(C)C)=O)=[C:8]([Cl:25])[CH:7]=1.Cl>C(OCC)C>[ClH:1].[Cl:26][C:2]([Cl:1])=[CH:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([Cl:25])[C:9]([O:10][CH2:11][CH2:12][CH2:13][NH2:14])=[C:22]([Cl:24])[CH:23]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22257137HCID 22257137, compound

Product 1

HCID 222571433-[4-(3,3-Dichloroprop-2-enyloxy)-2,6-dichlorophenoxy]propylamine hydrochlorideYield 75%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A stirred solution of 2.6 grams (0.0058 mole) of N-{3-[4-(3,3-dichloroprop-2-enyloxy)-2,6-dichlorophenoxy]propyl}(tert-butoxy)carboxamide in 10 mL of anhydrous diethyl ether was cooled to 0° C. and a 2N solution of hydrogen chloride in diethyl ether was added via a syringe. Upon completion of addition the reaction mixture was allowed to warm to ambient temperature where it stirred during an 18-hour period. A resultant solid precipitate was collected by filtration, yielding when dried, 1.25 grams of the subject compound. The filtrate was taken up in hexanes and allowed to stand during an 18-hour period, during which time a second crop of the subject compound precipitated from the filtrate. The precipitate was collected by filtration and dried, yielding an additional 0.83 gram of the subject compound.

Workup

  1. additionUpon completion of addition the reaction mixture
  2. filtrationA resultant solid precipitate was collected by filtration
  3. customyielding when
  4. customdried
  5. waitto stand during an 18-hour period, during which time
  6. customa second crop of the subject compound precipitated from the filtrate
  7. filtrationThe precipitate was collected by filtration
  8. customdried

Sources & evidence

ORD record
ord-cf7776e5324143caaa12f6ebfd0df359
Source dataset
uspto-grants-2006_01
Patent number
US06987194B2

Reaction notes

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