Iodine → HCID 66753972, compound

HRID 1896318Notes

Reaction equation

HRID 1896318 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]2[N:11]=[C:12]3[S:19][CH:18]=[CH:17][N:13]3[C:14](=[O:16])[CH:15]=2)=[CH:4][CH:3]=1.[I:20]I.O>CC#N>[Cl:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]2[N:11]=[C:12]3[S:19][CH:18]=[CH:17][N:13]3[C:14](=[O:16])[C:15]=2[I:20])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 807IodineHCID 962WaterHCID 13105884HCID 13105884, compound

Product 1

HCID 66753972HCID 66753972, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of Step 2 intermediate (3.0 g, 0.018 mmol), iodine (2.75 g, 0.018 mmol) and ceric ammonium nitrate (CAN) (4.93 g, 0.009 mmol) in CH3CN (30 ml) was stirred at 80° C. for 2 h. The reaction mixture was allowed to cool to room temperature. Distilled water (50 ml) was added to the residue obtained after concentration of the reaction mixture and stirred at room temperature for 1 h. The reaction mixture was filtered, dried under vacuum to give 5.30 g of the product as a light yellow solid; 1H NMR (300 MHz, CDCl3) δ 6.87 (d, J=15.6 Hz, 1H), 6.94 (d, J=4.8 Hz, 1H), 7.33 (d, J=9.0 Hz, 2H), 7.49 (d, J=8.4 Hz, 2H), 7.73 (d, J=15.6 Hz, 1H), 7.90 (d, J=4.8 Hz, 1H); ESI-MS (m/z) 289.37 (M+H)+.

Workup

  1. customobtained after concentration of the reaction mixture
  2. filtrationThe reaction mixture was filtered
  3. customdried under vacuum

Sources & evidence

ORD record
ord-4b339bb8ebb24434a4c76b48f91dbecd
Source dataset
uspto-grants-2013_08
Patent number
US08518955B2

Reaction notes

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