Thiomorpholine, 4-(2,6-difluoro-4-nitrophenyl)-, 1,1-dioxide → 4-(4-Amino-2,6-difluorophenyl)-1lambda~6~,4-thiazinane-1,1-dione

HRID 1826202Notes

Reaction equation

HRID 1826202 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[C:4]([F:11])[C:3]=1[N:12]1[CH2:17][CH2:16][S:15](=[O:19])(=[O:18])[CH2:14][CH2:13]1.[H][H]>[Ni].O1CCCC1>[O:19]=[S:15]1(=[O:18])[CH2:16][CH2:17][N:12]([C:3]2[C:4]([F:11])=[CH:5][C:6]([NH2:8])=[CH:7][C:2]=2[F:1])[CH2:13][CH2:14]1

Participants

5

Reactant 2

HCID 9922094Thiomorpholine, 4-(2,6-difluoro-4-nitrophenyl)-, 1,1-dioxideHCID 178418361HCID 178418361, compound

Product 1

HCID 98999344-(4-Amino-2,6-difluorophenyl)-1lambda~6~,4-thiazinane-1,1-dione

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To an autoclave was added 4-(2,6-difluoro-4-nitrophenyl)thiomorpholine 1,1-dioxide (Step 2, 7.0 kg, 24 moles, 1.0 eq). Raney Nickel (1.4 kg) was activated and suspended in tetrahydrofuran (4 L), and the slurry was added to the autoclave followed by additional tetrahydrofuran (66 L). The mixture was heated at 40° C. under a 40 psi hydrogen atmosphere until the reaction was complete. The mixture was then filtered, and the filtrate was directly used in the next step. A small portion of the filtrate can be concentrated and recrystallized in isopropanol to give the title compound in pure form, 1H NMR (DMSO-d6) (δ): 6.17 (m, 2H), 5.35 (s, 2H), 3.32 (m, 4H), 3.15 (m, 4H).

Workup

  1. additionthe slurry was added to the autoclave
  2. filtrationThe mixture was then filtered
  3. concentrationA small portion of the filtrate can be concentrated
  4. customrecrystallized in isopropanol

Sources & evidence

ORD record
ord-9ca9764fdcb44bf2a623a61ee9dcc17f
Source dataset
uspto-grants-2006_05
Patent number
US07049443B2

Reaction notes

Loading…