5,6-Dinitro-2-(2,2,2-trifluoroethyl)-2-(trifluoromethyl)-1,3-benzodioxole → HCID 53895814, compound

HRID 1081298Notes

Reaction equation

HRID 1081298 reaction equation
[N+:1]([C:4]1[C:21]([N+:22]([O-])=O)=[CH:20][C:7]2[O:8][C:9]([CH2:15][C:16]([F:19])([F:18])[F:17])([C:11]([F:14])([F:13])[F:12])[O:10][C:6]=2[CH:5]=1)([O-])=O.[H][H]>O1CCCC1>[NH2:22][C:21]1[C:4]([NH2:1])=[CH:5][C:6]2[O:10][C:9]([CH2:15][C:16]([F:19])([F:18])[F:17])([C:11]([F:12])([F:13])[F:14])[O:8][C:7]=2[CH:20]=1

Participants

4

Reactant 2

HCID 536607065,6-Dinitro-2-(2,2,2-trifluoroethyl)-2-(trifluoromethyl)-1,3-benzodioxoleHCID 178418361HCID 178418361, compound

Product 1

HCID 53895814HCID 53895814, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

339 g of the product from Example 17a were dissolved in 2,000 ml of tetrahydrofuran, and 20 g of catalyst (palladium on carbon, 5% by weight) were added. Hydrogenation was carried out with hydrogen at 25 to 30 bar for 13 hours at room temperature. The mixture was then filtered and the solvent stripped off in vacuo. A solid remained. The yield was 274 g (=96% of theory). 19F-NMR: -61.2 and -86.6 ppm; 1H-NMR: 3.02 ppm.

Workup

  1. filtrationThe mixture was then filtered

Sources & evidence

ORD record
ord-85c5a3b56c1a4e54b170baa95c149821
Source dataset
uspto-grants-1996_12
Patent number
US05585395

Reaction notes

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