N-Iodosuccinimide → HCID 49793319, compound

HRID 2369370Notes

Reaction equation

HRID 2369370 reaction equation
[I:1]N1C(=O)CCC1=O.[S:9]1[CH:13]=[C:12]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[N:11]=[CH:10]1>ClC(Cl)C>[I:1][C:13]1[S:9][CH:10]=[N:11][C:12]=1[NH:14][C:15](=[O:21])[O:16][C:17]([CH3:18])([CH3:20])[CH3:19]

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 53241636tert-butyl N-(1,3-thiazol-4-yl)carbamate

Product 1

HCID 49793319HCID 49793319, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

1033 mg (4.59 mmol) of N-iodosuccinimide are introduced into a solution of 800 mg (3.99 mmol) of tert-butyl N-(1,3-thiazol-4-yl)carbamate in 40 ml of dichloroethane, and the reaction mixture is heated under reflux for 2 h. After cooling, the mixture is washed twice with water and with saturated sodium thiosulfate solution. The combined organic phases are dried over sodium sulfate, evaporated in vacuo, and the residue is purified by flash chromatography on silica gel (eluent: cyclohexane/ethyl acetate 8/2 to 1/1), giving 1.19 g (3.43 mmol, 85%) of tert-butyl N-(5-iodo-1,3-thiazol-4-yl)carbamate as white crystals after crystallisation from diethyl ether; ESI-MS: m/e: 327 ([M+H]+).

Workup

  1. temperaturethe reaction mixture is heated
  2. temperatureunder reflux for 2 h
  3. temperatureAfter cooling
  4. washthe mixture is washed twice with water and with saturated sodium thiosulfate solution
  5. dry with materialThe combined organic phases are dried over sodium sulfate
  6. customevaporated in vacuo
  7. customthe residue is purified by flash chromatography on silica gel (eluent: cyclohexane/ethyl acetate 8/2 to 1/1)

Sources & evidence

ORD record
ord-1d3db42f930e4eb2acace99732148fc9
Source dataset
uspto-grants-2014_04
Patent number
US08703961B2

Reaction notes

Loading…