Iodine → HCID 59133070, compound

HRID 853079Notes

Reaction equation

HRID 853079 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[O:12][C:13]([F:16])([F:15])[F:14])[CH3:2].[Li]C(CC)C.[I:23]I.[Cl-].[NH4+]>C1COCC1.C1CCCCC1.O>[CH2:1]([O:3][C:4](=[O:17])[NH:5][C:6]1[C:7]([O:12][C:13]([F:14])([F:16])[F:15])=[CH:8][CH:9]=[CH:10][C:11]=1[I:23])[CH3:2]

Participants

8

Reactant 4

HCID 807IodineHCID 25517Ammonium ChlorideHCID 2781632ethyl N-[2-(trifluoromethoxy)phenyl]carbamateHCID 178418400CID 53628100

Product 1

HCID 59133070HCID 59133070, compoundYield 94.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8078CyclohexaneSolvent

Procedure

(2-Trifluoromethoxy-phenyl)-carbamic acid ethyl ester (42.4 g, 0.17 mol) was dissolved in THF (800 mL) and cooled to −70 ° C. sec-BuLi in cyclohexane (280 mL, 1.3 M) was added dropwise at this temperature with stirring. Stirring was continued for 1 h after addition was complete. A solution of iodine (43.2 g, 0.17 mol) in THF (160 mL) was added dropwise at −70 ° C. Stirring was continued for 1 h after addition was complete and the mixture was hydrolysed with saturated ammonium chloride solution. Water was added and the mixture was extracted with diethyl ether. The organic phases were washed with 40% sodium bisulfite, water, brine, pooled and dried with MgSO4. Evaporation of the solvent yielded the title compound, (60.2 g, 94%) as a colorless amorphous solid. (EI-MS: m/e=374.9 (M+))

Workup

  1. additionwas added dropwise at this temperature
  2. stirringStirring
  3. additionafter addition
  4. stirringStirring
  5. waitwas continued for 1 h
  6. additionafter addition
  7. extractionthe mixture was extracted with diethyl ether
  8. washThe organic phases were washed with 40% sodium bisulfite, water, brine
  9. dry with materialdried with MgSO4
  10. customEvaporation of the solvent

Sources & evidence

ORD record
ord-09e7138b26fc4ccf83235e4472c1ccd9
Source dataset
uspto-grants-2007_08
Patent number
US07253281B2

Reaction notes

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