Triethylamine → HCID 178524294, compound

HRID 1787991Notes

Reaction equation

HRID 1787991 reaction equation
[C:1]1([O:7][C:8](Cl)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH:11]1[CH:15]=[N:14][N:13]=[N:12]1.C(N(CC)CC)C>>[O:7]([C:8]([C:15]1[NH:14][N:13]=[N:12][N:11]=1)=[O:9])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 178418441HCID 178418441, compound

Product 1

HCID 178524294HCID 178524294, compound

Procedure

The title compound was prepared according to the procedure described in Tetrahedron Letters, 1977, 1935. Accordingly, phenylchloroformate (6.73 g, 43 mmol) was added dropwise into a solution of tetrazole (42.84 mmol, 3 wt % in 100 mL acetonitrile) containing triethylamine (4.35 g, 43 mmol) at 0° C. The mixture was stirred for 15 minutes and the solvent was removed without heating at reduced pressure. Ethyl acetate (80 mL) was added to the white solid and passed through a plug of silica gel, eluting with 3% triethylamine in ethyl acetate to afford phenoxycarbonyltetrazole in 85% yield (6.9 g). 1H-NMR (CDCl3): δ 7.34-7.54 (m, 5H); 9.34 (s, 1H).

Workup

  1. customThe title compound was prepared
  2. customthe solvent was removed
  3. temperaturewithout heating at reduced pressure
  4. additionEthyl acetate (80 mL) was added to the white solid
  5. washeluting with 3% triethylamine in ethyl acetate

Sources & evidence

ORD record
ord-335f8af1e0e84236bd5c51814b3a6896
Source dataset
uspto-grants-2009_03
Patent number
US07511133B2

Reaction notes

Loading…