Imidazole → tert-butyl N-(2-iodoethyl)carbamate

HRID 660519Notes

Reaction equation

HRID 660519 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CN=C1.[I:25]I.[C:27]([O:31][C:32](=[O:37])[NH:33][CH2:34][CH2:35]O)([CH3:30])([CH3:29])[CH3:28]>C(Cl)Cl>[C:27]([O:31][C:32](=[O:37])[NH:33][CH2:34][CH2:35][I:25])([CH3:30])([CH3:29])[CH3:28]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 2733206tert-butyl N-(2-hydroxyethyl)carbamate

Product 1

HCID 641024tert-butyl N-(2-iodoethyl)carbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of triphenylphosphine (40 g, 153 mmol) and imidazole (10.4 g, 153 mmol) in CH2Cl2 (375 mL) at RT, is added iodine (40.8 g, 160.6 mmol) portionwise. To this solution is added (2-hydroxyethyl)-carbamic acid tert-butyl ester (24.2 g, 150 mmol) in CH2Cl2 (75 mL) dropwise and the mixture allowed to stir at RT for 14 h. The mixture is then filtered and the filtrate concentrated to a crude red oil, which is partitioned between ether and sat. sodium thiosulfate. The aqueous phase is extracted with ether. The combined organic layers are reduced to 500 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 a crude red oil, which
  3. customis partitioned between ether and sat. 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-644e5737e3264143921c0ddeee9819aa
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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