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

HRID 1826201Notes

Reaction equation

HRID 1826201 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N:9]1[CH2:14][CH2:13][S:12](=[O:16])(=[O:15])[CH2:11][CH2:10]1.[N+:17]([O-])([OH:19])=[O:18].O>C(O)(=O)C>[F:8][C:4]1[CH:5]=[C:6]([N+:17]([O-:19])=[O:18])[CH:7]=[C:2]([F:1])[C:3]=1[N:9]1[CH2:10][CH2:11][S:12](=[O:16])(=[O:15])[CH2:13][CH2:14]1

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 962WaterHCID 9921212THIOMORPHOLINE, 4-(2,6-DIFLUOROPHENYL)-, 1,1-DIOXIDE

Product 1

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

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a suspension of 4-(2,6-difluorophenyl)thiomorpholine 1,1-dioxide (Step 1, 300 g, 1.21 mol) in 3 L of acetic acid, nitric acid (255 mL, ca. 6 mol, fuming, 90%) was added over 30 minutes at ambient temperature. A yellow precipitate forms within minutes and increases over time. The reaction was kept at room temperature for 18 hours and was then poured into 6 L of water. After stirring for 2 hours, the yellow suspension was filtered. The precipitate was washed with water (1.5 L×3) and ethanol (0.5 L×2) and dried at 50° C. overnight to give the title compound, 1H NMR (DMSO-d6) (δ): 8.05 (m, 2H), 3.69 (m, 4H), 3.26 (m, 4H).

Workup

  1. additionwas added over 30 minutes at ambient temperature
  2. waitA yellow precipitate forms within minutes
  3. temperatureincreases over time
  4. filtrationthe yellow suspension was filtered
  5. washThe precipitate was washed with water (1.5 L×3) and ethanol (0.5 L×2)
  6. customdried at 50° C. overnight

Sources & evidence

ORD record
ord-5975b40807884ab090d7a0b571317a4c
Source dataset
uspto-grants-2006_05
Patent number
US07049443B2

Reaction notes

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