4-(2-Fluoro-4-nitrophenyl)-1lambda~6~,4-thiazinane-1,1-dione → 4-(4-Amino-2-fluorophenyl)thiomorpholine 1,1-dioxide

HRID 56098Notes

Reaction equation

HRID 56098 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[N:11]1[CH2:16][CH2:15][S:14](=[O:18])(=[O:17])[CH2:13][CH2:12]1>C1COCC1.[Pd]>[NH2:8][C:6]1[CH:5]=[CH:4][C:3]([N:11]2[CH2:16][CH2:15][S:14](=[O:17])(=[O:18])[CH2:13][CH2:12]2)=[C:2]([F:1])[CH:7]=1

Participants

4

Reactant 1

HCID 159843694-(2-Fluoro-4-nitrophenyl)-1lambda~6~,4-thiazinane-1,1-dione

Product 1

HCID 435813994-(4-Amino-2-fluorophenyl)thiomorpholine 1,1-dioxide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(2-fluoro-4-nitrophenyl)1,1-dioxidothiomorpholine (4.00 g, 14.58 mmol) in THF (50 mL) was added Pd/C (1.30 g). The reaction mixture was stirred at rt under H2 for 12 h. The mixture was filtered, and the filtrate was concentrated in vacuo to give the title compound as an offwhite solid (2.40 g, 67%).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-4b4a2f8296c64eaa909b715e8b62270f
Source dataset
uspto-grants-2016_09
Patent number
US09434695B2

Reaction notes

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