Trifluoroacetic acid → HCID 21395794, compound

HRID 1973271Notes

Reaction equation

HRID 1973271 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1([C:10]([F:13])([F:12])[F:11])[O:7][CH:6]([CH2:8][OH:9])[CH2:5][O:4]1.[O:16]([C:18]#[N:19])[Na].FC(F)(F)C(O)=O>C(Cl)Cl>[F:13][C:10]([F:11])([F:12])[C:3]1([C:2]([F:1])([F:14])[F:15])[O:7][CH:6]([CH2:8][O:9][C:18](=[O:16])[NH2:19])[CH2:5][O:4]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 219971032,2-Bis(trifluoromethyl)-4-hydroxymethyl-1,3-dioxolaneHCID 178418852HCID 178418852, compound

Product 1

HCID 21395794HCID 21395794, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 15 grams of 2,2-bis(trifluoromethyl)-4-hydroxymethyl-1,3-dioxolane (0.0625 mols), 8.12 grams NaOCN (0.125 mols), and 75 ml methylene dichloride is stirred at 25°-35° C. while 14.3 grams trifluoroacetic acid is added dropwise. The mixture is stirred for 16 hours at 40° C. The product is filtered and the filter cake washed with methylene dichloride. The filtrate is washed with water and dried over Na2SO4 prior to vacuum-stripping. The reaction product is recrystallized from 1 part benzene to yield 2,2-bis(trifluoromethyl)-4-carbamoyloxymethyl-1,3-dioxolane (m.p. 52°-54° C.)

Workup

  1. additionis added dropwise
  2. filtrationThe product is filtered
  3. washthe filter cake washed with methylene dichloride
  4. washThe filtrate is washed with water
  5. dry with materialdried over Na2SO4
  6. customThe reaction product is recrystallized from 1 part benzene

Sources & evidence

ORD record
ord-92caa2051e0144a3b0e069b9145a2ab9
Source dataset
uspto-grants-1976_12
Patent number
US03996376

Reaction notes

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