Sulfuryl chloride → HCID 71757556, compound

HRID 2249383Notes

Reaction equation

HRID 2249383 reaction equation
[F:1][C:2]1[C:8]([CH3:9])=[CH:7][CH:6]=[C:5]([F:10])[C:3]=1[NH2:4].S(Cl)([Cl:14])(=O)=O>C(O)(=O)C>[Cl:14][C:7]1[CH:6]=[C:5]([F:10])[C:3]([NH2:4])=[C:2]([F:1])[C:8]=1[CH3:9]

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 150175362,6-Difluoro-3-methylaniline

Product 1

HCID 71757556HCID 71757556, compoundYield 65.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A solution of 2,6-difluoro-3-methylaniline (15 g, 105 mmol) in acetic acid (80 mL) was heated to 70° C. and a solution of sulfuryl chloride (16.0 g, 115 mmol) in acetic acid (40 mL) was added dropwise over 20 minutes. The temperature was maintained for 3 hours, then cooled and concentrated. The residue taken into water (100 mL) and the pH was adjusted to 9 with 2N sodium hydroxide and then extracted with methylene chloride (2×75 mL) and the combined extracts washed with brine, dried (sodium sulfate) and concentrated. The residue was distilled to give 4-chloro-2,6-difluoro-3-methylaniline (12.2 g, 69 mmol): bp 55°-65° C./55 mm.

Workup

  1. temperatureThe temperature was maintained for 3 hours
  2. temperaturecooled
  3. concentrationconcentrated
  4. extractionextracted with methylene chloride (2×75 mL)
  5. washthe combined extracts washed with brine
  6. dry with materialdried (sodium sulfate)
  7. concentrationconcentrated
  8. distillationThe residue was distilled

Sources & evidence

ORD record
ord-84a02a00bac14db08cb6a5b6aae1d6b4
Source dataset
uspto-grants-2008_01
Patent number
US07314849B2

Reaction notes

Loading…