Ammonia → HCID 19099824, compound

HRID 2253885Notes

Reaction equation

[F:1][C:2]([F:23])([F:22])[C:3]1([C:18]([F:21])([F:20])[F:19])[O:7][C:6]([CH2:9][CH2:10][C:11]#[N:12])([F:8])[C:5]([CH2:14][CH2:15][C:16]#[N:17])([F:13])[O:4]1.N.[H][H]>[Co].[Cr].[Co].O1CCCC1>[F:23][C:2]([F:1])([F:22])[C:3]1([C:18]([F:19])([F:20])[F:21])[O:4][C:5]([CH2:14][CH2:15][CH2:16][NH2:17])([F:13])[C:6]([CH2:9][CH2:10][CH2:11][NH2:12])([F:8])[O:7]1

Participants

Conditions

Temperature: 110 °C

Procedure

In a 1400 ml Hastelloy-C Shaker tube was charged the 2,2-bis(trifluoromethyl)-4,5-di(2-cyanoethyl)-4,5-difluoro-1,3-dioxolane of Example 43 (56.3 g, 0.16 mole), tetrahydrofuran (320 ml) and Raney-Cobalt catalyst (14.4 g). The tube was sealed and cool-evacuated. Ammonia (64 g, 3.765 mole) was transferred into the tube and the tube was pressurized with hydrogen gas to 500 psi. The tube was then heated to 110° C. and the hydrogen pressure was adjusted to 1500 psi. The heating was continued for 18 hrs at this temperature. After the tube was cooled, the product mixture was filtered to remove the catalyst, and solvent was removed in vacuo. The residue was distilled to give the desired product 46 g (80% yield) as a clear, colorless, viscous liquid, Bp. 80° C./0.06 mmHg. H-1 NMR (CDCl3): 3.02 (m, 4H), 2.30 (m, 4H), 1.97 (m, 4H), 1.50 (s, br, --NH2); F-19 NMR (CDCl3): -80.5 (m, 6F), [-108.8 (m, br, trans), -110.6 (m, br cis) (2F total)].

Workup

customThe tube was sealed
customcool-evacuated
temperatureAfter the tube was cooled
filtrationthe product mixture was filtered
customto remove the catalyst, and solvent
customwas removed in vacuo
distillationThe residue was distilled

Sources & evidence

ORD record: ord-3ee2a8f5c9314140b0f3404880518a10
Source dataset: uspto-grants-1993_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05233058

Reaction notes

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