Hexamethylenetetramine → 2-Cyano-7-methoxybenzofuran-4-carbaldehyde

HRID 2084810Notes

Reaction equation

HRID 2084810 reaction equation
[C:1]([C:3]1[O:4][C:5]2[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[CH:8][C:6]=2[CH:7]=1)#[N:2].C1N2CN3CN(C2)CN1C3.FC(F)(F)[C:26](O)=[O:27]>>[C:1]([C:3]1[O:4][C:5]2[C:6](=[C:8]([CH:26]=[O:27])[CH:9]=[CH:10][C:11]=2[O:12][CH3:13])[CH:7]=1)#[N:2]

Participants

4

Reactant 3

HCID 4101HexamethylenetetramineHCID 6422Trifluoroacetic acidHCID 2985567-Methoxybenzofuran-2-carbonitrile

Product 1

HCID 227342992-Cyano-7-methoxybenzofuran-4-carbaldehydeYield 21%

Conditions

Temperature
65 °C

Procedure

A mixture of 2-cyano-7-methoxybenzofuran (4.17 g), hexamethylenetetramine (3.38 g), and trifluoroacetic acid (62 ml) was stirred at 60 to 70° C. for one hour. The mixture was concentrated and the residue was purified by silica gel column chromatography (toluene/ethyl acetate=20/1) to give Compound IIi (1.02 g, 21%) as colorless crystals.

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was purified by silica gel column chromatography (toluene/ethyl acetate=20/1)

Sources & evidence

ORD record
ord-2ce0866e80a54e93bd9e6a58721e9370
Source dataset
uspto-grants-2004_04
Patent number
US06716987B1

Reaction notes

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