Sodium Iodide → HCID 68432210, compound

HRID 889245Notes

Reaction equation

HRID 889245 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13](Br)[CH:12]=[C:11]([F:16])[C:10]=1[N:17]1[S:21](=[O:23])(=[O:22])[NH:20][C:19](=[O:24])[CH2:18]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Na+].[I-:26].CN[C@@H]1CCCC[C@H]1NC>O1CCOCC1.[Cu]I>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([I:26])[CH:12]=[C:11]([F:16])[C:10]=1[N:17]1[S:21](=[O:23])(=[O:22])[NH:20][C:19](=[O:24])[CH2:18]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 5238Sodium IodideHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 68431695HCID 68431695, compound

Product 1

HCID 68432210HCID 68432210, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 5-(2-benzyloxy-4-bromo-6-fluorophenyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one (1.0 g, 2.21 mmol), NaI (1.18 g, 7.87 mmol), CuI (91 mg, 0.48 mmol) and (1R,2R)—N,N′-dimethylcyclohexane-1,2-diamine (136 mg, 0.96 mmol) in dioxane (15.5 mL) is heated at 140° C. for 1.5 h in a microwave. The reaction mixture is filtered through Celite and washed with additional dioxane. It is then concentrated to a smaller volume and used directly in the next step: MS (M−H)−=461.

Workup

  1. filtrationThe reaction mixture is filtered through Celite
  2. washwashed with additional dioxane
  3. concentrationIt is then concentrated to a smaller volume

Sources & evidence

ORD record
ord-a9fef62ab19448b687e917cffefa6536
Source dataset
uspto-grants-2012_08
Patent number
US08252820B2

Reaction notes

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