Water → HCID 19603718, compound

HRID 1604656Notes

Reaction equation

HRID 1604656 reaction equation
[C:1]([C:5]1[N:6]=[C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([C:19]4[NH:23][N:22]=[N:21][N:20]=4)=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].I[CH2:25][C:26]1[CH:36]=[CH:35][CH:34]=[CH:33][C:27]=1[C:28]([O:30][CH2:31][CH3:32])=[O:29].C(=O)([O-])[O-].[K+].[K+].O>CC(=O)CC>[C:1]([C:5]1[N:6]=[C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([C:19]4[N:23]=[N:22][N:21]([CH2:25][C:26]5[CH:36]=[CH:35][CH:34]=[CH:33][C:27]=5[C:28]([O:30][CH2:31][CH3:32])=[O:29])[N:20]=4)=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:4])([CH3:2])[CH3:3].[C:1]([C:5]1[N:6]=[C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([C:19]4[N:23]([CH2:25][C:26]5[CH:36]=[CH:35][CH:34]=[CH:33][C:27]=5[C:28]([O:30][CH2:31][CH3:32])=[O:29])[N:22]=[N:21][N:20]=4)=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 22184407Ethyl 2-(iodomethyl)benzoateHCID 178441405HCID 178441405, compound

Product 2

HCID 19603718HCID 19603718, compoundHCID 19603742HCID 19603742, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 5-[2-(4-tert-butylthiazol-2-yl)benzofuran-5-yl]-1H-tetrazole (1.55 g), ethyl 2-iodomethylbenzoate (1.67 g) and potassium carbonate (1.80 g) in 2-butanone (15 ml) was stirred under reflux for 5 hours. After being cooled, the resulting mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to column chromatography on silica gel and eluted with a mixture of toluene and ethyl acetate. The fractions containing object compound were combined and concentrated under reduced pressure to give 5-[2-(4-tert-butylthiazol-2-yl)benzofuran-5-yl]-2-[2-(ethoxycarbonyl)phenylmethyl]-2H-tetrazole (2.05 g) and 5-[2-(4-tert-butylthiazol-2-yl)benzofuran-5-yl]-1-[2-(ethoxycarbonyl)phenylmethyl]-1H-tetrazole (0.24 g).

Workup

  1. temperatureunder reflux for 5 hours
  2. temperatureAfter being cooled
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. washeluted with a mixture of toluene and ethyl acetate
  8. additionThe fractions containing object compound
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4cfc9535bbff483fbee11661b3f6c195
Source dataset
uspto-grants-1999_11
Patent number
US05994378

Reaction notes

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