Ammonia → HCID 19099826, compound

HRID 2253887Notes

Reaction equation

HRID 2253887 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]1([C:16]([F:19])([F:18])[F:17])[O:7][CH:6]([CH2:8][CH2:9][C:10]#[N:11])[CH:5]([CH2:12][CH2:13][C:14]#[N:15])[O:4]1.N.[H][H]>[Co].[Cr].[Co].O1CCCC1>[F:21][C:2]([F:1])([F:20])[C:3]1([C:16]([F:17])([F:18])[F:19])[O:4][CH:5]([CH2:12][CH2:13][CH2:14][NH2:15])[CH:6]([CH2:8][CH2:9][CH2:10][NH2:11])[O:7]1

Participants

7

Reactant 3

HCID 222AmmoniaHCID 19099831HCID 19099831, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 19099826HCID 19099826, compoundYield 42.8%

Reagents, catalysts & solvents 3

HCID 104730CobaltCatalystHCID 11332432Hastelloy CCatalystHCID 8028TetrahydrofuranSolvent

Procedure

The compound of Example 56 (9.72 g, 0.031 mole) was mixed with tetrahydrofuran (60 ml), Raney-Cobalt (2.8 g) and ammonia (12 g, 0.706 mole) in a 360 ml Hastelloy-C Shaker tube. The tube was pressurized with hydrogen to 500 psi at room temperature. The tube was then heated at 110° C. for 18 hrs while the hydrogen pressure was adjusted to 1500 psi under the reaction process. The product mixture was filtered first, then was distilled to give the desired product 4.3 g as a clear, colorless liquid. Bp 85° C./0.02 mmHg. H-1 NMR (CDCl3): 3.98 (s, br, 2H), 2.76 (t, J=6 Hz, 4H), 1.80-1.50 (m, 8H), 1.30 (s, br, 4H); F-19 NMR (CDCl3): -81.1 (s, 6F).

Workup

  1. filtrationThe product mixture was filtered first
  2. distillationwas distilled

Sources & evidence

ORD record
ord-8cac2d71123e43578c9daa9ee87c806b
Source dataset
uspto-grants-1993_08
Patent number
US05233058

Reaction notes

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