[Hydroxy(tosyloxy)iodo]benzene → HCID 57513836, compound

HRID 2368424Notes

Reaction equation

HRID 2368424 reaction equation
[F:1][C:2]([CH3:16])([CH3:15])[C:3](=O)[CH2:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=1)=[O:6].CC1C=CC(S(OI(O)C2C=CC=CC=2)(=O)=O)=CC=1.[NH2:36][C:37]([NH2:39])=[S:38]>CC#N>[NH2:39][C:37]1[S:38][C:4]([C:5]([C:7]2[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=2)=[O:6])=[C:3]([C:2]([F:1])([CH3:16])[CH3:15])[N:36]=1

Participants

5

Reactant 3

HCID 325434[Hydroxy(tosyloxy)iodo]benzeneHCID 2723790ThioureaHCID 57435368HCID 57435368, compound

Product 1

HCID 57513836HCID 57513836, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 4-Fluoro-1-(4-fluoro-phenyl)-4-methyl-pentane-1,3-dione (900 mg) and Koser's reagent (4.2 g) in MeCN (20 mL) was heated at 80° C. for 50 min. The mixture was cooled to RT, and thiourea (820 mg) was added. The mixture was heated at 80° C. for 3 h., cooled to RT and partitioned between ethyl acetate and aq. KOH. The organic extract was dried over MgSO4, concentrated and chromatographed to give the title compound. m/z 283.2 (MH+). 1H NMR (DMSO-d6) 7.81 (dd, J=8, 4 Hz, 2H), 7.73 (s, 2H), 7.32 (t, J=8 Hz, 2H), 1.61 (d, J=20 Hz, 6H).

Workup

  1. temperatureThe mixture was cooled to RT
  2. temperatureThe mixture was heated at 80° C. for 3 h.
  3. temperaturecooled to RT
  4. custompartitioned between ethyl acetate and aq. KOH
  5. extractionThe organic extract
  6. dry with materialwas dried over MgSO4
  7. concentrationconcentrated
  8. customchromatographed

Sources & evidence

ORD record
ord-f3c32b860d004d69963ae311eb9ffae0
Source dataset
uspto-grants-2014_04
Patent number
US08703761B2

Reaction notes

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