3-Chlorobenzoic Acid → HCID 21393535, compound

HRID 461365Notes

Reaction equation

HRID 461365 reaction equation
[CH3:1][N:2]1[C:6](=[O:7])[C:5]([Cl:9])([Cl:8])[C:4]([Cl:11])([Cl:10])[S:3]1.C(Cl)(Cl)Cl.ClC1C=CC=C(C(OO)=[O:24])C=1.ClC1C=C(C=CC=1)C(O)=O>C(=O)=O>[CH3:1][N:2]1[C:6](=[O:7])[C:5]([Cl:8])([Cl:9])[C:4]([Cl:10])([Cl:11])[S:3]1=[O:24]

Participants

6

Reactant 4

HCID 4473-Chlorobenzoic AcidHCID 6212Chloroform2×HCID 70297m-Chloroperbenzoic acidHCID 123247444,4,5,5-Tetrachloro-2-methyl-1,2-thiazolidin-3-one

Product 1

HCID 21393535HCID 21393535, compound

Reagents, catalysts & solvents 1

HCID 280Carbon DioxideSolvent

Procedure

To a solution of 2.55g. (0.01 mole) of 2-methyl-4,4,5,5-tetrachloro-3-isothiazolidinone in 10 ml. of chloroform at 0° is added a solution of 2.03g. (0.01 mole) of m-chloroperbenzoic acid (85% Technical) in 60 ml. of chloroform. The mixture is allowed to warm to room temperature and stand over a weekend. The solution is cooled in dry ice. White solid (m-chlorobenzoic acid) separates (0.91g.) and is removed by filtration. The filtrate is washed in a separatory funnel with 50 ml. of water containing 0.4g. of sodium bicarbonate. The chloroform solution is separated and dried over magnesium sulfate. Evaporation gives 2.54g. of crude product as a white solid.

Workup

  1. waitstand over a weekend
  2. customis removed by filtration
  3. washThe filtrate is washed in a separatory funnel with 50 ml
  4. customThe chloroform solution is separated
  5. dry with materialdried over magnesium sulfate
  6. customEvaporation
  7. customgives 2.54g

Sources & evidence

ORD record
ord-009bb48a07424e378f49841748f4b36b
Source dataset
uspto-grants-1977_12
Patent number
US04062859

Reaction notes

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