Hydroxylamine → 2-Thiabicyclo[3.2.2]non-5-en-3-one oxime

HRID 464643Notes

Reaction equation

HRID 464643 reaction equation
[CH:1]1[CH2:7][CH2:6][CH2:5][CH:4]=[CH:3][CH:2]=1.[C:8](Cl)(Cl)=[S:9].C1CCCCC1.[NH2:18][OH:19]>C(Cl)Cl.O>[CH:4]12[CH2:5][CH2:6][C:7](=[CH:2][CH2:3]1)[CH2:1][C:8](=[N:18][OH:19])[S:9]2

Participants

7

Reactant 4

HCID 787HydroxylamineHCID 8078CyclohexaneHCID 10040ThiophosgeneHCID 199691,3-Cycloheptadiene

Product 1

HCID 867391662-Thiabicyclo[3.2.2]non-5-en-3-one oxime

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 29 g (0.3 m) of 1,3-cycloheptadiene, 46 g (0.4 m) of thiophosgene, and 25 ml of cyclohexane was heated under reflux for 24 hours, then stripped of volatiles under reduced pressure. The oily residue was taken up in 150 ml of methylene chloride and stirred with 1.5 m of hydroxylamine in 200 ml of water at room temperature for three days. The separated organic layer was dried over magnesium sulfate and stripped to yield 26.7 g of viscous oil. Purification by dry column chromatography using silica gel and 1:4::ether:hexane as eluent. There was obtained 14 g of yellow solid. Recrystallization of 2 g portion from 1:1 ether-hexane yielded 1.4 g of the title compound as white crystals, m. 130°-132° C.

Workup

  1. temperatureunder reflux for 24 hours
  2. dry with materialThe separated organic layer was dried over magnesium sulfate

Sources & evidence

ORD record
ord-754600ee85d34f2098b845d6aab14c79
Source dataset
uspto-grants-1985_10
Patent number
US04548929

Reaction notes

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