Trifluoroacetic acid → HCID 21395826, compound

HRID 1973273Notes

Reaction equation

HRID 1973273 reaction equation
[Cl:1][C:2]([F:15])([F:14])[C:3]1([C:10]([Cl:13])([F:12])[F:11])[O:7][CH:6]([CH2:8][OH:9])[CH2:5][O:4]1.[O-:16][C:17]#[N:18].[Na+].FC(F)(F)C(O)=O>C(Cl)Cl>[Cl:13][C:10]([F:11])([F:12])[C:3]1([C:2]([Cl:1])([F:14])[F:15])[O:7][CH:6]([CH2:8][O:9][C:17](=[O:16])[NH2:18])[CH2:5][O:4]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 517096Sodium CyanateHCID 21395814HCID 21395814, compound

Product 1

HCID 21395826HCID 21395826, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

A sample of 15 grams of 2,2-bis(chlorodifluoromethyl)-4-hydroxymethyl-1,3-dioxolane (0.055 mols) is dissolved in 75 ml methylene chloride and 7.16 grams of sodium cyanate (0.11 mols) is added. Trifluoroacetic acid, 12.6 grams, (0.11 mols) is added dropwise with stirring at 23°-33° C. The temperature is then raised to 40° C. and stirring continued for 18 hours. The product is filtered and the filtrate washed with water until neutral. Vacuum stripping gives a quantitative yield of crude products which solidified partly. Filtration and recrystallization from a mixture of benzene-hexane and once from cyclohexane yields 2,2-bis(chlorodifluoromethyl)-4-carbamoyloxymethyl-1,3-dioxolane (m.p. 56°-57° C.)

Workup

  1. stirringstirring
  2. filtrationThe product is filtered
  3. washthe filtrate washed with water until neutral
  4. customVacuum stripping gives a quantitative yield of crude products which
  5. filtrationFiltration and recrystallization
  6. additionfrom a mixture of benzene-hexane

Sources & evidence

ORD record
ord-99a7ab19c35a4283ad495211fdd5d49b
Source dataset
uspto-grants-1976_12
Patent number
US03996376

Reaction notes

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