4-Iodobenzamide → HCID 23279242, compound

HRID 1250388Notes

Reaction equation

HRID 1250388 reaction equation
[I:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=O)=[CH:4][CH:3]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:20])=CC=1>O1CCCC1>[I:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[S:20])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 775614-IodobenzamideHCID 87949Lawesson's reagent

Product 1

HCID 23279242HCID 23279242, compoundYield 134.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2.1 g of 4-iodobenzamide, 30 ml of tetrahydrofuran, and 2 g of Lawesson's reagent was heated to reflux for 1 hour. It was partitioned between toluene and 10% aqueous sodium carbonate solution. The organic phase was dried and evaporated. The crude product was passed over a plug of silica gel using acetone/hexane 1:1 for elution. Crystallization from methylene chloride/hexane gave 1.75 g of yellow crystals with m.p. 163-165° C.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 1 hour
  3. customIt was partitioned between toluene and 10% aqueous sodium carbonate solution
  4. customThe organic phase was dried
  5. customevaporated
  6. washfor elution
  7. customCrystallization from methylene chloride/hexane

Sources & evidence

ORD record
ord-0503ddfd24a64c9f8edcbad6d2e18075
Source dataset
uspto-grants-2002_01
Patent number
US06337344B1

Reaction notes

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