Nitric Acid → Thiomorpholine, 4-(2,6-difluoro-4-nitrophenyl)-, 1,1-dioxide

HRID 395261

Reaction equation

HRID 395261 reaction equation
[O:1]=[S:2]1(=[O:27])[CH2:7][CH2:6][N:5]([C:8]2[C:13]([F:14])=[CH:12][C:11](N3C[C@H](CNC(=O)C)OC3=O)=[CH:10][C:9]=2[F:26])[CH2:4][CH2:3]1.[N+:28]([O-:31])(O)=[O:29].O>C(O)(=O)C>[F:14][C:13]1[CH:12]=[C:11]([N+:28]([O-:31])=[O:29])[CH:10]=[C:9]([F:26])[C:8]=1[N:5]1[CH2:4][CH2:3][S:2](=[O:27])(=[O:1])[CH2:7][CH2:6]1

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 962WaterHCID 9931003Pnu-288034

Product 1

HCID 9922094Thiomorpholine, 4-(2,6-difluoro-4-nitrophenyl)-, 1,1-dioxideYield 94.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a suspension of the product of example 1 (300 g, 1.21 mol) in 3 L of acetic acid, nitric acid (255 mL, ca. 6 mol, fuming, 90%) is added over 30 min at room temperature. Yellow precipitate is formed within minutes and increases over time. The reaction is kept at room temperature for 18 hours, before it is poured into 6 L of water. After stirred for 2 hours, the yellow suspension is filtered. The precipitate is washed with water (1.5 L×3) and EtOH (0.5 L×2) and dried in oven at 50° C. overnight to give 333 g (94%) of the title compound as a solid.

Workup

  1. additionis added over 30 min at room temperature
  2. customYellow precipitate is formed within minutes
  3. temperatureincreases over time
  4. filtrationthe yellow suspension is filtered
  5. washThe precipitate is washed with water (1.5 L×3) and EtOH (0.5 L×2)
  6. customdried in oven at 50° C. overnight

Sources & evidence

ORD record
ord-005797f02363405c9b410f8b0a949391
Source dataset
uspto-grants-2003_08
Patent number
US06605609B2

Linked notes

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