Dimethylformamide → 3-Acetimido-5-ethoxy-4-iodo-benzaldehyde

HRID 1990834Notes

Reaction equation

HRID 1990834 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:11][CH2:12][CH3:13])[C:9]=1[I:10])[CH:5]=[O:6].[C:14](Cl)(=[O:16])[CH3:15].C(N(C(C)C)CC)(C)C.CN(C=[O:31])C>>[C:14]1(=[O:16])[N:1]([C:2]2[CH:3]=[C:4]([CH:7]=[C:8]([O:11][CH2:12][CH3:13])[C:9]=2[I:10])[CH:5]=[O:6])[C:15]1=[O:31]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 587063533-Amino-5-ethoxy-4-iodo-benzaldehyde2×

Product 1

HCID 866076313-Acetimido-5-ethoxy-4-iodo-benzaldehydeYield 35%

Conditions

Temperature
50 °C

Procedure

To a solution of 3-amino-5-ethoxy-4-iodo-benzaldehyde (0.27 g, 0.93 mmol, 1.0 equiv; intermediate 25) and acetyl chloride (0.138 mL, 0.153 g, 1.95 mmol, 2.1 equiv) in anhydrous DMF (5 mL) was added diisopropylethylamine (0.48 mL, 0.36 g, 2.78 mmol, 3.0 equiv) and the mixture stirred at 50° C. for 48 h. Removal of the solvent under reduced pressure and purification of the crude reaction mixture with column chromatography on silica eluting with a gradient of heptane/ethyl acetate (4:1→1:1) yielded 0.11 g (35%) of the title compound. 1H NMR (300 MHz, CDCl3): δ 1.51 (t, J=7.0 Hz, 3H), 2.29 (s, 3H), 4.19 (q, J=7.0 Hz, 2H), 7.06 (s, 1H), 7.76 (br s, 1H), 8.42 (s, 1H), 9.96 (s, 1H). MS (ISP): 334.0 [M+H]+.

Workup

  1. customRemoval of the solvent
  2. customunder reduced pressure and purification of the crude
  3. customreaction mixture with column chromatography on silica eluting with a gradient of heptane/ethyl acetate (4:1→1:1)

Sources & evidence

ORD record
ord-71931424d0eb4a34b0e442b6632551d7
Source dataset
uspto-grants-2010_01
Patent number
US07645753B2

Reaction notes

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