Toluene → HCID 54220385, compound

HRID 1447958Notes

Reaction equation

HRID 1447958 reaction equation
Br[N:2]1[CH2:5][C:4]([CH2:8][Br:9])([CH2:6][Br:7])[C:3]1=[O:10].C1(C)C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:7][CH2:6][C:4]1([CH2:8][Br:9])[CH2:5][NH:2][C:3]1=[O:10]

Participants

4

Reactant 2

HCID 1140TolueneHCID 53647688HCID 53647688, compound

Product 1

HCID 54220385HCID 54220385, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A 22.4 g (0.067 mole) sample of the 1-bromo-3,3-bis(bromomethyl)-2-azetidinone was dissolved in 450 ml carbon tetrachloride. The insoluble residue (2.0 g) was discarded. A 7 ml (6.07 g, 0.067 mole) portion of toluene was added to the stirred solution. The reaction mixture was irradiated by a 275 watt General Electric Sunlamp and allowed to reflux for one hour. The reaction mixture was decanted hot from a small amount of residue on the stirrer and flask wall and then cooled in ice. White crystals were collected on a filter and dried in vacuo to yield 12.1 g of product. Mother liquor with a few seed crystals was kept cold overnight to yield a second crop of 1.0 g. Total yield of 13.1 g or 76.6% of 3,3-bis(bromomethyl)-2-azetidinone was recovered.

Workup

  1. customThe reaction mixture was irradiated by a 275 watt General Electric Sunlamp
  2. temperatureto reflux for one hour
  3. customThe reaction mixture was decanted hot from a small amount of residue on the stirrer and flask wall
  4. temperaturecooled in ice
  5. customWhite crystals were collected on
  6. filtrationa filter
  7. customdried in vacuo

Sources & evidence

ORD record
ord-e54d9d79d05c4d139e07448bcdf8b732
Source dataset
uspto-grants-1979_12
Patent number
US04179298

Reaction notes

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