Iodine → HCID 11018176, compound

HRID 891004Notes

Reaction equation

HRID 891004 reaction equation
[CH2:1]([O:8][CH2:9][N:10]1[C:14](=[O:15])[C:13]([C:16]2[C:24]3[C:19](=[N:20][CH:21]=[CH:22][CH:23]=3)[N:18]([C@@H:25]3[O:42][C@H:41]([CH2:43][O:44][C:45](=[O:47])[CH3:46])[C@@H:36]([O:37][C:38](=[O:40])[CH3:39])[C@H:31]([O:32][C:33](=[O:35])[CH3:34])[C@H:26]3[O:27][C:28](=[O:30])[CH3:29])[CH:17]=2)=[C:12]([C:48]2[C:56]3[C:51](=[CH:52][CH:53]=[CH:54][CH:55]=3)[NH:50][CH:49]=2)[C:11]1=[O:57])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.II>C1C=CC=CC=1.C(OCC)(=O)C.[Hg]>[CH2:1]([O:8][CH2:9][N:10]1[C:11](=[O:57])[C:12]2[C:48]3[C:56]4[C:51](=[CH:52][CH:53]=[CH:54][CH:55]=4)[NH:50][C:49]=3[C:17]3[N:18]([C@@H:25]4[O:42][C@H:41]([CH2:43][O:44][C:45](=[O:47])[CH3:46])[C@@H:36]([O:37][C:38](=[O:40])[CH3:39])[C@H:31]([O:32][C:33](=[O:35])[CH3:34])[C@H:26]4[O:27][C:28](=[O:30])[CH3:29])[C:19]4[N:20]=[CH:21][CH:22]=[CH:23][C:24]=4[C:16]=3[C:13]=2[C:14]1=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 807IodineHCID 11767899HCID 11767899, compound

Product 1

HCID 11018176HCID 11018176, compound

Reagents, catalysts & solvents 3

HCID 23931MercuryCatalystHCID 241BenzeneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the compound of Example 1b (0.409 mmol), dissolved in 500 ml of benzene, there is added iodine (4.90 mmol). The mixture is irradiated in a quartz reactor equipped with an immersible medium-pressure mercury-vapour U.V. lamp of 400 W for 1 hour 30 minutes. The solvent is evaporated off; the crude reaction product is taken up in ethyl acetate and washed with aqueous sodium thiosulphite solution and then with saturated aqueous sodium chloride solution. The organic phase is dried over magnesium sulphate and filtered, and the solvent is evaporated off. After purification by chromatography on silica gel (cyclohexane/ethyl acetate: 3/2), the expected product is isolated.

Workup

  1. customThe mixture is irradiated in a quartz reactor
  2. customThe solvent is evaporated off
  3. customthe crude reaction product
  4. washwashed with aqueous sodium thiosulphite solution
  5. dry with materialThe organic phase is dried over magnesium sulphate
  6. filtrationfiltered
  7. customthe solvent is evaporated off
  8. customAfter purification by chromatography on silica gel (cyclohexane/ethyl acetate: 3/2)

Sources & evidence

ORD record
ord-d93914047a5d4bef8ce9a3f1548ff2d9
Source dataset
uspto-grants-2006_02
Patent number
US07001906B2

Reaction notes

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