Hydroxylamine, O-(3-chloro-2-propenyl)-, hydrochloride → HCID 178449940, compound

HRID 2308578Notes

Reaction equation

HRID 2308578 reaction equation
C[O-].[Na+].Cl.[Cl:5][CH:6]=[CH:7][CH2:8][O:9][NH2:10].[C:11]([CH:16]1[C:21](=[O:22])[CH2:20][CH:19]([CH2:23][CH:24]([S:26][CH2:27][CH3:28])[CH3:25])[CH2:18][C:17]1=[O:29])(=O)[CH2:12][CH2:13][CH3:14]>CO>[Cl:5][CH:6]=[CH:7][CH2:8][O:9][N:10]=[C:11]([C@H:16]1[C:21](=[O:22])[CH2:20][C@H:19]([CH2:23][CH:24]([S:26][CH2:27][CH3:28])[CH3:25])[CH2:18][C:17]1=[O:29])[CH2:12][CH2:13][CH3:14]

Participants

5

Reactant 3

HCID 158057Hydroxylamine, O-(3-chloro-2-propenyl)-, hydrochlorideHCID 28347542-Butyryl-5-[2-(ethylthio)propyl]-1,3-cyclohexanedioneHCID 10942334Sodium Methoxide

Product 1

HCID 178449940HCID 178449940, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.38 g of sodium methoxide, 10 ml of methanol, and 1.0 g of 3-chloroallyloxyamine hydrochloride (H2NOCH2CH=CHCl) were admixed together and then stirred for 10 minutes at room temperature. 2 g of 2-butyryl-5-(2-ethylthiopropyl)cyclohexane-1,3-dione was added and the resulting mixture stirred for about two days at room temperature. The mixture was then concentrated by evaporation and the concentrate mixed with 60 ml of diethyl ether and 40 ml of water. The ether layer was extracted with 40 ml of aqueous 2 wt. % sodium hydroxide solution, washed with 20 ml of water, dried over anhydrous magnesium sulfate and evaporated affording a minor amount of the title compound as the trans isomer.

Workup

  1. stirringthe resulting mixture stirred for about two days at room temperature
  2. concentrationThe mixture was then concentrated by evaporation
  3. additionthe concentrate mixed with 60 ml of diethyl ether and 40 ml of water
  4. extractionThe ether layer was extracted with 40 ml of aqueous 2 wt. % sodium hydroxide solution
  5. washwashed with 20 ml of water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-f14811ed5d074a11a7ea681453140aa3
Source dataset
uspto-grants-1987_09
Patent number
USRE032489

Reaction notes

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