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

HRID 395262Notes

Reaction equation

HRID 395262 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>[Ni].C1COCC1>[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

4

Reactant 1

HCID 9922094Thiomorpholine, 4-(2,6-difluoro-4-nitrophenyl)-, 1,1-dioxide

Product 1

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

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
40 °C

Procedure

To an autoclave is added the product of example 2 (7.0 kg, 24 moles, 1.0 eq). Raney Nickel (1.4 kg) is activated and suspended in 4 L of THF. The slurry is added to the autoclave followed by additional THF (66 L). The mixture is heated at 40° C. and under 40 psi H2 till completion. The mixture is filtered and the filtrate is directly used in the next step. A small portion of the filtrate is concentrated and recrystallized in isopropanol to give the title compound.

Workup

  1. additionThe slurry is added to the autoclave
  2. filtrationThe mixture is filtered
  3. concentrationA small portion of the filtrate is concentrated
  4. customrecrystallized in isopropanol

Sources & evidence

ORD record
ord-a7398e05070b4c1686247e74b4a2d7dd
Source dataset
uspto-grants-2003_08
Patent number
US06605609B2

Reaction notes

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