Sodium Iodide → 4-(Iodomethyl)-2-phenylthiazole

HRID 394274Notes

Reaction equation

HRID 394274 reaction equation
[I-:1].[Na+].Cl[CH2:4][C:5]1[N:6]=[C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[S:8][CH:9]=1.C(N)(=S)C1C=CC=CC=1.ClCC(CCl)=O>CC(C)=O.O.COC(C)(C)C>[I:1][CH2:4][C:5]1[N:6]=[C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[S:8][CH:9]=1

Participants

8

Reactant 4

HCID 5238Sodium IodideHCID 107931,3-DichloroacetoneHCID 2369694-(Chloromethyl)-2-phenyl-1,3-thiazoleHCID 683563Thiobenzamide

Product 1

HCID 131965984-(Iodomethyl)-2-phenylthiazoleYield 99.5%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

2 g (13.35 mmol) of sodium iodide were added to a solution of 0.56 g (2.67 mmol) of 4-chloromethyl-2-phenyl-thiazole (prepared from thiobenzamide and 1,3-dichloroacetone in analogy to the procedure described in example 4 a]) in 10 ml of acetone and the suspension was stirred at reflux for 2 hours. After cooling to ambient temperature, 30 ml of tert-butyl methyl ether and 10 ml of water were added and the mixture was transferred to a separatory funnel. The organic phase was washed with water and brine, dried with anhydrous sodium sulfate and finally evaporated, leaving 0.8 g of 4-iodomethyl-2-phenyl-thiazole as light yellow solid (99% of theory).

Workup

  1. temperatureat reflux for 2 hours
  2. customthe mixture was transferred to a separatory funnel
  3. washThe organic phase was washed with water and brine
  4. dry with materialdried with anhydrous sodium sulfate
  5. customfinally evaporated

Sources & evidence

ORD record
ord-c1e79178e7da4afda2393de26009660f
Source dataset
uspto-grants-2004_10
Patent number
US06809110B2

Reaction notes

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