Ethyl orthoformate → HCID 21220901, compound

HRID 1584798Notes

Reaction equation

HRID 1584798 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH3:11])[C:5]2[O:9][CH:8]=[CH:7][C:6]=2[CH:10]=1.[CH2:12](OC(OCC)OCC)C.[N-:22]=[N+:23]=[N-:24].[Na+]>C(O)(=O)C>[CH3:11][C:4]1[C:5]2[O:9][CH:8]=[CH:7][C:6]=2[CH:10]=[C:2]([N:1]2[CH:12]=[N:24][N:23]=[N:22]2)[CH:3]=1

Participants

5

Reactant 3

HCID 31214Ethyl orthoformateHCID 33557Sodium AzideHCID 21220844HCID 21220844, compound

Product 1

HCID 21220901HCID 21220901, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 5-amino-7-methyl-benzofuran (350 mg) and triethylorthoformate (0.42 ml) in glacial acetic acid (10 ml) was heated at 80° for 1 hour. Sodium azide (470 mg) was added and stirring continued at 80° C. for 4 hours. The mixture was partitioned between ethyl acetate (25 ml) and 8% sodium bicarbonate solution (40 ml), the aqueous was further extracted with ethyl acetate (2×25 ml). The combined organic extracts were washed with hydrochloric acid (2M:25 ml), dried (MgSO4), and evaporated in vacuo. The residue was purified by FCC eluting (with ether-hexane (3:1) to give the title compound as a white solid (174 mg), m.p. 118°.

Workup

  1. temperaturewas heated at 80° for 1 hour
  2. customThe mixture was partitioned between ethyl acetate (25 ml) and 8% sodium bicarbonate solution (40 ml)
  3. extractionthe aqueous was further extracted with ethyl acetate (2×25 ml)
  4. washThe combined organic extracts were washed with hydrochloric acid (2M:25 ml)
  5. dry with materialdried (MgSO4)
  6. customevaporated in vacuo
  7. customThe residue was purified by FCC
  8. washeluting (with ether-hexane (3:1)

Sources & evidence

ORD record
ord-454c08ca0ecf49c6b431cdf58c05b02d
Source dataset
uspto-grants-1999_08
Patent number
US05935972

Reaction notes

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