p-Toluenesulfonyl azide → HCID 86641203, compound

HRID 1644778Notes

Reaction equation

HRID 1644778 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:4]=[C:5]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.CC1C=CC(S([N:31]=[N+:32]=[N-])(=O)=O)=CC=1.C1CCN2C(=NCCC2)CC1>C(#N)C>[F:1][C:2]([F:19])([F:20])[C:3]1[CH:4]=[C:5]([C:13](=[N+:31]=[N-:32])[C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:6]=[C:7]([C:9]([F:11])([F:12])[F:10])[CH:8]=1

Participants

5

Reactant 3

HCID 13661p-Toluenesulfonyl azideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 42552891Ethyl [3,5-bis(trifluoromethyl)phenyl]acetate

Product 1

HCID 86641203HCID 86641203, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of ethyl 3,5-bis(trifluoromethyl)phenylacetate (Step M, 26.0 g, 87 mmol) and 4-methylbenzenesulfonyl azide (Step L, 18.0 g, 91 mmol) in dry acetonitrile (150 mL) was added DBU (14.3 mL, 95 mmol) dropwise at −10° C. over 15 min with stirring. The mixture was stirred at −10° C. for a further 0.5 hr. The solvent was removed and the residue was partitioned between ether and water. The organic layer was washed with aqueous NaHCO3, brine, dried over Mg2SO4, and the solvent was removed. The residue was chromatographed (eluted with 9:1 hexane:ethyl acetate) to afforded a yellow solid. 1H-NMR (CDCl3): δ: 8.0 (2H, s), 7.68 (1H, s), 4.41 (2H, d, J=7.1 Hz), 1.40 (3H, t, J=7.1 Hz).

Workup

  1. stirringThe mixture was stirred at −10° C. for a further 0.5 hr
  2. customThe solvent was removed
  3. customthe residue was partitioned between ether and water
  4. washThe organic layer was washed with aqueous NaHCO3, brine
  5. dry with materialdried over Mg2SO4
  6. customthe solvent was removed
  7. customThe residue was chromatographed
  8. wash(eluted with 9:1 hexane:ethyl acetate)
  9. customto afforded a yellow solid

Sources & evidence

ORD record
ord-8d12d6ee4c3c455b948b09345f05cd74
Source dataset
uspto-grants-2012_02
Patent number
US08124633B2

Reaction notes

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