Pyridine → HCID 19818995, compound

HRID 1195215Notes

Reaction equation

HRID 1195215 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1([C:11]([F:14])([F:13])[F:12])[O:7][CH:6]([C:8](O)=[O:9])[CH2:5][O:4]1.N1C=CC=CC=1.S(Cl)([Cl:25])=O>>[F:1][C:2]([F:16])([F:15])[C:3]1([C:11]([F:14])([F:13])[F:12])[O:7][CH:6]([C:8]([Cl:25])=[O:9])[CH2:5][O:4]1

Participants

4

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 15123681HCID 15123681, compound

Product 1

HCID 19818995HCID 19818995, compoundYield 81%

Procedure

2,2-Bis(trifluoromethyl)-1,3-dioxolan-4-oyl chloride was prepared from 2,2-bis(trifluoromethyl)-4-carboxy-1,3-dioxolane (see U.S. patent application 07/401,668, filed Aug. 30, 1989) (25.4 g, 0.1 mole). To this substrate was added pyridine (3.16 g, 0.04 mole) followed by thionyl chloride (14.3 g, 0.12 mole), with external cooling to maintain the pot at ambient temperature. When the addition was complete, the reaction mixture was heated slowly to 70° C. for 1.5 hour, then at 90° to 100° C. for 0.5 hour. The product was distilled from the reaction mixture, a clear colorless liquid, 22.0 g (81% yield) was obtained. Bp. 50° C./10 mm. 1H-NMR (Neat): δ 5.23 (t, J=7.0 Hz, 1H), 4.73 (m, 2H); 19F NMR (neat): -80.5 (q, J=8.5 Hz, 3F), -81.5 (q, J=8.5 Hz, 3F). Anal. Calc. for C6H3ClF6O3 : C: 26.44, H: 1.11, F: 41.83, Cl: 13.00; Found: C: 26.13, H: 1.11, F: 41.44, Cl: 13.38. ##STR6##

Workup

  1. temperaturewith external cooling
  2. additionWhen the addition
  3. temperaturethe reaction mixture was heated slowly to 70° C. for 1.5 hour
  4. distillationThe product was distilled from the reaction mixture
  5. customa clear colorless liquid, 22.0 g (81% yield) was obtained

Sources & evidence

ORD record
ord-881ae4d4a7724fcb95878ff19379e9f9
Source dataset
uspto-grants-1992_05
Patent number
US05110938

Reaction notes

Loading…