Imidazole → HCID 68840725, compound

HRID 660650Notes

Reaction equation

HRID 660650 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CN=C1.[I:25]I.O[CH2:28][CH2:29][CH2:30][N:31]([CH:41]([CH3:43])[CH3:42])[S:32]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)(=[O:34])=[O:33]>C(Cl)Cl>[I:25][CH2:28][CH2:29][CH2:30][N:31]([CH:41]([CH3:43])[CH3:42])[S:32]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)(=[O:34])=[O:33]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 54916387HCID 54916387, compound

Product 1

HCID 68840725HCID 68840725, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of triphenylphosphine (4.4 g, 16.6 mmol) and imidazole (1.2 g, 16.7 mmol) in CH2Cl2 (40 mL) at RT, is added iodine (4.3 g, 17 mmol) portionwise. To this solution is added N-(3-hydroxypropyl)-N-isopropylbenzenesulfonamide (4.2 g, 16.5 mmol) in CH2Cl2 (8 mL) dropwise and the mixture allowed to stir at RT for 18 h. The mixture is then filtered and the filtrate concentrated to an oil, which is partitioned between ether and saturated sodium thiosulfate. The aqueous phase is extracted with ether. The combined organic layers are reduced to 10 mL and then filtered through a plug of silica, eluting with hexane. Evaporation of solvent affords the title compound.

Workup

  1. filtrationThe mixture is then filtered
  2. concentrationthe filtrate concentrated to an oil, which
  3. customis partitioned between ether and saturated sodium thiosulfate
  4. extractionThe aqueous phase is extracted with ether
  5. filtrationfiltered through a plug of silica
  6. washeluting with hexane
  7. customEvaporation of solvent

Sources & evidence

ORD record
ord-74518678219e4d77b35b2eb460bd3cd3
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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