Nitrogen → HCID 18439222, compound

HRID 456932Notes

Reaction equation

HRID 456932 reaction equation
[CH3:1][O:2][C:3]1[C:4]([I:14])=[C:5]([C:9]([I:13])=[CH:10][C:11]=1[I:12])[C:6]([OH:8])=[O:7].[Si](C=[N+]=[N-])(C)(C)[CH3:16].N#N>CCOCC.CO>[CH3:1][O:2][C:3]1[C:4]([I:14])=[C:5]([C:9]([I:13])=[CH:10][C:11]=1[I:12])[C:6]([O:8][CH3:16])=[O:7]

Participants

6

Reactant 3

HCID 947NitrogenHCID 167693TrimethylsilyldiazomethaneHCID 18439217HCID 18439217, compound

Product 1

HCID 18439222HCID 18439222, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

In a 3-neck 250 mL round-bottom flask fitted with a thermometer and a condenser, 3-methoxy-2,4,6-triiodobenzoic acid (10.38 g) was dissolved in a 2:1 mixture of Et2O and methanol at 0° C. A 2.0 M hexanes solution of TMSCHN2 was added dropwise until yellow color persisted and N2 bubbling stopped. The reaction mixture was stirred for 30 minutes and quenched with glacial acetic acid. Solvents and excess AcOH were removed in vacuo for 18 h to give the desired ester as a white solid which was used in the next step without any further purification. Yield 11.07 g (˜100% crude).

Workup

  1. customquenched with glacial acetic acid
  2. customSolvents and excess AcOH were removed in vacuo for 18 h

Sources & evidence

ORD record
ord-c9486bf3be634bfbbec14a7afafac660
Source dataset
uspto-grants-2007_03
Patent number
US07186797B2

Reaction notes

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