Sulfuryl chloride → HCID 22996498, compound

HRID 429970Notes

Reaction equation

HRID 429970 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][CH:17]=1)[N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:6][CH3:7].C([Li])CCC.[S:23](Cl)([Cl:26])(=[O:25])=[O:24]>C1COCC1>[C:11]([O:10][C:8]([N:5]([CH2:6][CH3:7])[C:4]1[CH:15]=[CH:16][CH:17]=[C:2]([S:23]([Cl:26])(=[O:25])=[O:24])[CH:3]=1)=[O:9])([CH3:14])([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 24648Sulfuryl chlorideHCID 22996319HCID 22996319, compoundHCID 178418339Butyllithium

Product 1

HCID 22996498HCID 22996498, compoundYield 93.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

3-Bromo-N-tert-butoxycarbonyl-N-ethylaniline (3.0 mmol) was dissolved in freshly distilled THF (25 ml) under a N2 atmosphere. The solution was chilled to −78° C. and butyl lithium (1.8 ml, 2.0 M solution in cyclohexane, 3.6 mmol) was added. After 35 minutes, sulfuryl chloride (0.30 ml, 3.6 mmol) was added over ˜2 minutes. The reaction was stirred for 5 minutes at −78° C. then was allowed to warm to room temperature. After 30 minutes at room temperature the reaction was cooled to −78° C. and quenched with a saturated ammonium chloride solution. The THF was removed by evaporation and the resulting residue was and partitioned between EtOAc and H2O. The aqueous phase was extracted with EtOAc and the combined organic phases were washed with H2O and brine before being dried with Na2SO4. The solvent was removed in vacuo to give 900 mg of crude product. HPLC showed the material to be ˜80% pure and it was used as is. LC/MS (ES): 320.1 (M+1).

Workup

  1. temperatureto warm to room temperature
  2. temperatureAfter 30 minutes at room temperature the reaction was cooled to −78° C.
  3. customquenched with a saturated ammonium chloride solution
  4. customThe THF was removed by evaporation
  5. custompartitioned between EtOAc and H2O
  6. extractionThe aqueous phase was extracted with EtOAc
  7. washthe combined organic phases were washed with H2O and brine
  8. dry with materialbefore being dried with Na2SO4
  9. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-9cba7c3094b84cf1a14c37d87572a9c2
Source dataset
uspto-grants-2001_11
Patent number
US06319946B1

Reaction notes

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