1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 18672362, compound

HRID 1058254Notes

Reaction equation

HRID 1058254 reaction equation
C1C=CC(P([N:15]=[N+:16]=[N-:17])(C2C=CC=CC=2)=O)=CC=1.C1CCN2C(=NCCC2)CC1.[Cl:29][C:30]1[CH:31]=[CH:32][C:33]([I:38])=[C:34]([CH:37]=1)[CH2:35]O>CN(C=O)C>[Cl:29][C:30]1[CH:31]=[CH:32][C:33]([I:38])=[C:34]([CH:37]=1)[CH2:35][N:15]=[N+:16]=[N-:17]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 818020(5-Chloro-2-iodophenyl)methanol

Product 1

HCID 18672362HCID 18672362, compoundYield 107.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

DPPA (0.442 mL, 2.05 mmol) followed by DBU (0.306 mL, 2.05 mmol) were added to a stirred solution of 5-chloro-2-iodobenzyl alcohol (500 mg, 1.86 mmol) in DMF (10 mL) at 0° C. and the reaction mixture was warmed to room temperature. After 16 h the mixture was warmed to 70° C. for 2 hr. The reaction was then concentrated and the residue was partitioned between EtOAc and 10% NaHCO3. The organic layer was washed with water and brine, dried (Na2SO4) and evaporated to give 5-chloro-2-iodobenzylazide (588 mg): 1H NMR (CDCl3, 400 MHz) δ 4.43 (s, 2H), 7.03 (dd, J=2.6, 8.4 Hz, 1H), 7.39 (d, J=2.6, 1H), 7.78 (d, J=8.4 Hz, 1H).

Workup

  1. temperatureAfter 16 h the mixture was warmed to 70° C. for 2 hr
  2. concentrationThe reaction was then concentrated
  3. customthe residue was partitioned between EtOAc and 10% NaHCO3
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried (Na2SO4)
  6. customevaporated

Sources & evidence

ORD record
ord-29f6bd8c9d93420db2155607cd656b18
Source dataset
uspto-grants-2003_02
Patent number
US06515011B2

Reaction notes

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