Iodine chloride → HCID 58959113, compound

HRID 915871Notes

Reaction equation

HRID 915871 reaction equation
[Cl:1][C:2]1[C:3]2[CH:10]=[CH:9][N:8]([C@@H:11]3[O:21][C@H:20]([CH2:22][O:23][C:24](=[O:26])[CH3:25])[C@@H:15]([O:16][C:17](=[O:19])[CH3:18])[C@H:12]3[O:13][CH3:14])[C:4]=2[N:5]=[CH:6][N:7]=1.[I:27]Cl>C(Cl)Cl>[Cl:1][C:2]1[C:3]2[C:10]([I:27])=[CH:9][N:8]([C@@H:11]3[O:21][C@H:20]([CH2:22][O:23][C:24](=[O:26])[CH3:25])[C@@H:15]([O:16][C:17](=[O:19])[CH3:18])[C@H:12]3[O:13][CH3:14])[C:4]=2[N:5]=[CH:6][N:7]=1

Participants

4

Reactant 2

HCID 24640Iodine chlorideHCID 58959121HCID 58959121, compound

Product 1

HCID 58959113HCID 58959113, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of compound 5.5 (1.25 g, 3.26 mmol) in CH2Cl2 (80 mL), a 1.0 M solution of ICl in CH2Cl2 (8.12 mmol) was added at room temperature and the resulting dark brown solution was stirred for 4 hr at room temperature. The solvents were evaporated in vacuo at 25° C.-35° C. and the residue was dried under high vacuum for 30 min. A light brown sticky material was obtained which was purified by flash column chromatography using gradient of pure CH2Cl2 to 1.5% MeOH in CH2Cl2 to afford the desired compound 5.6 (1.1 g, 66%) as a white solid.

Workup

  1. customThe solvents were evaporated in vacuo at 25° C.-35° C.
  2. customthe residue was dried under high vacuum for 30 min
  3. customA light brown sticky material was obtained which
  4. customwas purified by flash column chromatography

Sources & evidence

ORD record
ord-c35eec0bd8c94fe0aeb7f71ef61f6acd
Source dataset
uspto-grants-2007_09
Patent number
US07268119B2

Reaction notes

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