Iodine → HCID 68918735, compound

HRID 968863Notes

Reaction equation

HRID 968863 reaction equation
[CH2:1]([O:3][C:4](=[O:34])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][C:15]2[N:19]([CH2:20][CH2:21][CH3:22])[C:18](=[O:23])[N:17]([C:24]3[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=3)[N:16]=2)=[CH:9][CH:8]=1)[CH3:2].[I:35]I>S([O-])([O-])(=O)=O.[Ag+2].C(O)C>[CH2:1]([O:3][C:4](=[O:34])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][C:15]2[N:19]([CH2:20][CH2:21][CH3:22])[C:18](=[O:23])[N:17]([C:24]3[CH:29]=[CH:28][C:27]([C:30]([F:31])([F:32])[F:33])=[CH:26][CH:25]=3)[N:16]=2)=[CH:9][C:8]=1[I:35])[CH3:2]

Participants

5

Reactant 2

HCID 807Iodine2×HCID 68918281HCID 68918281, compound

Product 1

HCID 68918735HCID 68918735, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 178418844HCID 178418844, compoundCatalyst2×HCID 702EthanolSolvent

Procedure

A mixture of (4-{2-[5-Oxo-4-propyl-1-(4-trifluoromethyl-phenyl)-4,5-dihydro-1H-[1,2,4]triazol-3-yl]-ethyl}-phenoxy)acetic acid ethyl ester (180 mg, 0.38 mmol), iodine (105 mg, 0.42 mmol), silver sulfate (131 mg, 0.42 mmol) and ethanol were stirred at room temperature. After 3.5 h, more iodine (86 mg) and silver sulfate (106 mg) were added and stirred for another 0.5 h. The reaction mixture was quenched with water and extracted with ethyl acetate. The combined organic extracts were washed with water, brine, dried and evaporated to dryness to afford the product (217 mg, 95%). 1HMR (400 MHz, CDCl3) δ 8.15 (d, 2H, J=8.4 Hz), 7.73 (s, 1H), 7.67 (d, 2H, J=8.4 Hz), 7.18 (m, 1H), 6.67 (d, 1H, J=8.0 Hz), 4.66 (s, 2H), 4.26 (q, 2H, J=7.6 Hz), 3.68 (t, 2H, J=7.3 Hz), 3.05 (t, 2H, J=7.4 Hz), 2.82 (t, 2H, J=7.3 Hz), 1.7 (m, 2H), 1.29 (t, 3H, J=7.6 Hz), 0.96 (t, 3H, J=7.6 Hz); ESMS m/z (relative intensity) 604.2 (M+H+, 100).

Workup

  1. stirringstirred for another 0.5 h
  2. customThe reaction mixture was quenched with water
  3. extractionextracted with ethyl acetate
  4. washThe combined organic extracts were washed with water, brine
  5. customdried
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-dc7a4230f6c2487ab716505917301415
Source dataset
uspto-grants-2007_12
Patent number
US07304062B2

Reaction notes

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