Triethyl orthoacetate → 2-(4-Iodophenyl)-5-methyl-[1,3,4]oxadiazole

HRID 31411

反応式

HRID 31411 の反応式
[I:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([NH:8][NH2:9])=[O:7])=[CH:4][CH:3]=1.[C:12](OCC)(OCC)(OCC)[CH3:13]>>[I:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]2[O:7][C:12]([CH3:13])=[N:9][N:8]=2)=[CH:4][CH:3]=1

参加物

3

反応物 2

HCID 66221Triethyl orthoacetateHCID 3061044-Iodobenzenecarbohydrazide2 回

生成物 1

HCID 6765692-(4-Iodophenyl)-5-methyl-[1,3,4]oxadiazole

反応条件

温度
130 °C

実験手順

Triethyl orthoacetate (10 ml) was added to 4-iodo-benzoic acid hydrazide (Intermediate 14) (0.55 g, 2.1 mmol) and heated under nitrogen at 130° C. for 3 hours. The triethyl orthoacetate was removed in vacuo and the residue partitioned between ethyl acetate (30 ml) and water (30 ml). The organic layer was washed with water (50 ml), brine (50 ml), dried over magnesium sulfate filtered and the solvent removed in vacuo. The residue was purified by silica SPE cartridge (10 g) eluting with 20:1 cyclohexane/ethyl acetate v:v to 5:1 cyclohexane/ethyl acetate v:v. The desired product was obtained as a white solid (0.31 g, 1.1 mmol).

後処理

  1. customThe triethyl orthoacetate was removed in vacuo
  2. customthe residue partitioned between ethyl acetate (30 ml) and water (30 ml)
  3. washThe organic layer was washed with water (50 ml), brine (50 ml)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent removed in vacuo
  7. customThe residue was purified by silica SPE cartridge (10 g)
  8. washeluting with 20:1 cyclohexane/ethyl acetate v

出典と根拠

ORDレコード
ord-83ed388e738c4ac3a3d041d293b05383
出典データセット
uspto-grants-2008_09
特許番号
US07425555B2

関連ノート

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