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

HRID 723832Notes

Reaction equation

HRID 723832 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%) is added over 30 minutes at ambient temperature. A yellow precipitate forms within minutes and increases over time. The reaction is kept at room temperature for 18 h and is then poured into 6 L of water. After stirring for 2 h, the yellow suspension is filtered. The precipitate is 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. additionis added over 30 minutes at ambient temperature
  2. waitA yellow precipitate forms within minutes
  3. temperatureincreases over time
  4. filtrationthe yellow suspension is filtered
  5. washThe precipitate is washed with water (1.5 L×3) and ethanol (0.5 L×2)
  6. customdried at 50° C. overnight

Sources & evidence

ORD record
ord-df37dc9fcffc49419aea90672cb74ce7
Source dataset
uspto-grants-2006_11
Patent number
US07141588B2

Reaction notes

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