Iodine → HCID 178522802, compound

HRID 574656Notes

Reaction equation

HRID 574656 reaction equation
[CH:1]([NH:14][C:15]([C:17]1[C:18]([OH:28])=[N:19][C:20]([N:23]2[CH:27]=[CH:26][CH:25]=[N:24]2)=[N:21][CH:22]=1)=[O:16])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O=[N+]([O-])[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[Ce+4].[NH4+].[NH4+].[I:56]I>C(#N)C>[CH:1]([NH:14][C:15]([C:17]1[C:18]([OH:28])=[N:19][C:20]([N:23]2[CH:27]=[C:26]([I:56])[CH:25]=[N:24]2)=[N:21][CH:22]=1)=[O:16])([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 807IodineHCID 180504Ceric ammonium nitrateHCID 178522801HCID 178522801, compound2×

Product 1

HCID 178522802HCID 178522802, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
85 °C

Procedure

The product of step B, compound 1-1-b, (3.2 g, 8.6 mmol) was dissolved in acetonitrile (100 mL), and treated with CAN (6.62 g, 12.1 mmol) and I2 (1.42 g, 5.6 mmol). The reaction mixture was stirred for 16 h at 85° C. The resulting mixture was concentrated, diluted with 50 mL of water, stirred for 20 min and filtered. The solid filtrate was dried under vacuum to provide the product, 1-1-c (3.6 g, 84%). 1H NMR (300 MHz, DMSO-d6) δ 6.22-6.24 (d, J=6.6, 1H), 7.22-7.39 (m, 11H), 7.55-7.74 (m, 1H), 8.07 (m, 1H), 8.47 (m, 1H), 8.71 (s, 1H), 10.49 (s, 1H). LC-MS 498[MH]+.

Workup

  1. concentrationThe resulting mixture was concentrated
  2. additiondiluted with 50 mL of water
  3. stirringstirred for 20 min
  4. filtrationfiltered
  5. customThe solid filtrate was dried under vacuum

Sources & evidence

ORD record
ord-cf8095ed048c40e784fafdab67d7ff1a
Source dataset
uspto-grants-2015_05
Patent number
US09034851B2

Reaction notes

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