Dimethylformamide → 3-Iodobenzamide

HRID 1473164Notes

Reaction equation

HRID 1473164 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5](O)=[O:6].C(Cl)(=O)C(Cl)=O.C[N:18](C=O)C>C1COCC1>[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([NH2:18])=[O:6]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 120603-Iodobenzoic acidHCID 65578Oxalyl chloride

Product 1

HCID 2024253-IodobenzamideYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Iodobenzoic acid (2.00 g, 8.06 mmol) was dissolved in THF (20 mL) then oxalyl chloride (1.4 mL, 16 mmol) and DMF (0.05 mL) were added and the resulting mixture stirred for 2 hours. The volatiles were evaporated under reduced pressure and the residue was dissolved in THF (20 mL) and concentrated aqueous ammonia (10 mL). After 60 minutes water (200 mL) was added and after a further 30 minutes the resulting precipitate was collected by filtration and air dried to give the title compound (I142) (1.97 g, 99% yield) as a white powder; 1H NMR (400 MHz, d4MeOH) δ 8.23 (t, J=1.8 Hz, 1H), 7.90 (ddd, J=7.9, 1.7, 1.0 Hz, 1H), 7.86 (ddd, J=7.8, 1.7, 1.0 Hz, 1H), 7.24 (t, J=7.8 Hz, 1H). LCMS Method C: rt 5.29 min, m/z 248.1 [M+H]+.

Workup

  1. customThe volatiles were evaporated under reduced pressure
  2. dissolutionthe residue was dissolved in THF (20 mL)
  3. additionAfter 60 minutes water (200 mL) was added and after a further 30 minutes the resulting precipitate
  4. filtrationwas collected by filtration and air
  5. customdried

Sources & evidence

ORD record
ord-c96c9773673b4adb8255ea5551bd774c
Source dataset
uspto-grants-2015_04
Patent number
US09012461B2

Reaction notes

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