Ethyl formate → 2-(N-Formylaminomethyl)benzoxazole

HRID 1736666Notes

Reaction equation

HRID 1736666 reaction equation
[NH2:1][CH2:2][C:3]1[O:4][C:5]2[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=2[N:7]=1.[CH:12](OCC)=[O:13]>>[CH:12]([NH:1][CH2:2][C:3]1[O:4][C:5]2[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=2[N:7]=1)=[O:13]

Participants

3

Reactant 2

HCID 8025Ethyl formateHCID 14155281-(1,3-Benzoxazol-2-yl)methanamine

Product 1

HCID 229128102-(N-Formylaminomethyl)benzoxazole

Procedure

A mixture of 4.29 g (28.9 mmol) of 2-(aminomethyl)benzoxazole (PREPARATION 6) and 20 ml of ethyl formate is heated at 80° for 2 hr, after which the excess ethyl formate is removed under reduced pressure. The residue is chromatographed on silica gel (350 ml) eluting with methanol/dichloromethane (2/98), the appropriate fractions are pooled and concentrated to give the product, which is crystallized from dichloromethane/hexane to give the title compound, mp 98°-99°; MS (m/z) at 176; IR 1655, 1621, 1519, 1241, 750 cm-1 ; NMR (CDCl3) 4.81, 6.45, 7.36. 7.53, 7.70, 8.39 δ.

Workup

  1. temperatureis heated at 80° for 2 hr
  2. customafter which the excess ethyl formate is removed under reduced pressure
  3. customThe residue is chromatographed on silica gel (350 ml)
  4. washeluting with methanol/dichloromethane (2/98)
  5. concentrationconcentrated
  6. customto give the product, which
  7. customis crystallized from dichloromethane/hexane

Sources & evidence

ORD record
ord-5b7b120dfb2048dbbd4ced276d9fe779
Source dataset
uspto-grants-1996_07
Patent number
US05541324

Reaction notes

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