Sodium Iodide → HCID 86736403, compound

HRID 614449Notes

Reaction equation

HRID 614449 reaction equation
S(C1C=CC(C)=CC=1)(O[CH2:5][C@H:6]1[C@@H:9]([NH:10][C:11](=[O:27])[CH:12]([NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:8](=[O:28])[NH:7]1)(=O)=O.[I-:36].[Na+]>CC(C)=O>[C:23]([O:22][C:20]([NH:19][CH:12]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:11]([NH:10][C@H:9]1[C:8](=[O:28])[NH:7][C@H:6]1[CH2:5][I:36])=[O:27])=[O:21])([CH3:26])([CH3:25])[CH3:24]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 86736404HCID 86736404, compound

Product 1

HCID 86736403HCID 86736403, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 2 g (3.98 mmol) of product from Example 20, 6 g (40 mmol) of sodium iodide and 150 ml of acetone is thoroughly degassed with argon and then heated at 55°-60° for seven hours. The mixture is cooled to room temperature and the acetone is evaporated. The residue is partitioned between ethyl acetate and water. The organic phase is separated and washed with aqueous sodium thiosulfate and saline. The dried solution is evaporated to give 1.48 g (81%) of the title product.

Workup

  1. customis thoroughly degassed with argon
  2. temperatureheated at 55°-60° for seven hours
  3. customthe acetone is evaporated
  4. customThe residue is partitioned between ethyl acetate and water
  5. customThe organic phase is separated
  6. washwashed with aqueous sodium thiosulfate and saline
  7. customThe dried solution is evaporated

Sources & evidence

ORD record
ord-fa3070cc3c3f45199255b90fcd977431
Source dataset
uspto-grants-1979_03
Patent number
US04144333

Reaction notes

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