N-Iodosuccinimide → HCID 86640503, compound

HRID 1960108Notes

Reaction equation

HRID 1960108 reaction equation
C1C(=O)N([I:8])C(=O)C1.[C:9]1([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:14]=[CH:13][C:12]([CH2:15][NH:16][C:17]2[CH:22]=[C:21]([F:23])[CH:20]=[C:19]([F:24])[C:18]=2[N+:25]([O-:27])=[O:26])=[CH:11][CH:10]=1>CC(O)=O>[C:9]1([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:10]=[CH:11][C:12]([CH2:15][NH:16][C:17]2[CH:22]=[C:21]([F:23])[C:20]([I:8])=[C:19]([F:24])[C:18]=2[N+:25]([O-:27])=[O:26])=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 67361471HCID 67361471, compound

Product 1

HCID 86640503HCID 86640503, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
70 °C

Procedure

NIS (7.9 g, 35.1 mmol) was added to a solution of N-(biphenyl-4-ylmethyl)-3,5-difluoro-2-nitroaniline (10.86 g, 31.9 mmol) in AcOH (150 mL). After heating at 70° C. for 2 h, the reaction mixture was concentrated and partitioned between EtOAc and saturated aqueous NaHCO3. The organic phase was washed with brine, dried (Na2SO3) and concentrated. Recrystallization from DCM/hexanes afforded the desired product as a red solid.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. custompartitioned between EtOAc and saturated aqueous NaHCO3
  3. washThe organic phase was washed with brine
  4. dry with materialdried (Na2SO3)
  5. concentrationconcentrated
  6. customRecrystallization from DCM/hexanes

Sources & evidence

ORD record
ord-128bb6a9ec88407387eda1824762495d
Source dataset
uspto-grants-2013_04
Patent number
US08410284B2

Reaction notes

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