N-Iodosuccinimide → HCID 87586268, compound

HRID 729229Notes

Reaction equation

HRID 729229 reaction equation
[CH:1]([NH:3][C:4]1[CH:8]=[CH:7][S:6][CH:5]=1)=[O:2].[I:9]N1C(=O)CCC1=O>ClC(Cl)(Cl)Cl>[I:9][C:5]1[S:6][CH:7]=[CH:8][C:4]=1[NH:3][CH:1]=[O:2]

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 12571917HCID 12571917, compound

Product 1

HCID 87586268HCID 87586268, compoundYield 90.5%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
2.5 °C

Procedure

3-Formylamino-thiophene (21 g), N-iodosuccinimide (37.2 g) and tetrachlormethane (200 ml) were refluxed together for 3 hours. The reaction mixture was cooled to 0-5° C. and filtered. The solids were dissolved in ethyl acetate, washed three times with sodium hydroxide (10% solution), washed with brine and dried over sodium sulfate. Evaporation of the solvents and chromatography of the residue over silica gel (hexane:ethyl acetate 2:1) yielded 37.8 g of product (m.p. 100-107° C.) which was directly used in Step B.

Workup

  1. filtrationfiltered
  2. dissolutionThe solids were dissolved in ethyl acetate
  3. washwashed three times with sodium hydroxide (10% solution)
  4. washwashed with brine
  5. dry with materialdried over sodium sulfate
  6. customEvaporation of the solvents and chromatography of the residue over silica gel (hexane:ethyl acetate 2:1)

Sources & evidence

ORD record
ord-bd2180724a99487a82a0234227448a76
Source dataset
uspto-grants-2009_09
Patent number
US07582589B2

Reaction notes

Loading…