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

HRID 1991245Notes

Reaction equation

HRID 1991245 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 is 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) is activated and suspended in tetrahydrofuran (4 L), and the slurry is added to the autoclave followed by additional tetrahydrofuran (66 L). The mixture is heated at 40° C. under a 40 psi hydrogen atmosphere until the reaction is complete. The mixture is then filtered, and the filtrate is 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 is added to the autoclave
  2. filtrationThe mixture is then filtered
  3. concentrationA small portion of the filtrate can be concentrated
  4. customrecrystallized in isopropanol

Sources & evidence

ORD record
ord-38e5d6a75b7048208f68968f240402aa
Source dataset
uspto-grants-2010_01
Patent number
US07645781B2

Reaction notes

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