Water → 3-(4-Benzyloxyphenyl)-5-bromomethyl-[1,2,4]thiadiazole

HRID 453107ノート

反応式

HRID 453107 の反応式
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:19]=[C:18]([CH2:20]O)[S:17][N:16]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Br)(Br)[Br:23].O>C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:19]=[C:18]([CH2:20][Br:23])[S:17][N:16]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 962WaterHCID 24614Phosphorus tribromideHCID 59549522[3-(4-Benzyloxyphenyl)-[1,2,4]thiadiazol-5-yl]-methanol

生成物 1

HCID 595495273-(4-Benzyloxyphenyl)-5-bromomethyl-[1,2,4]thiadiazole収率 70%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
120 °C

実験手順

To a solution of [3-(4-benzyloxyphenyl)-[1,2,4]thiadiazol-5-yl]-methanol (0.052 g, 0.17 mmol) in toluene (5 ml) was added PBr3 (0.027 ml, 0.26 mmol) and the resulting reaction mixture was refluxed at 120° C. for 15 min. After the completion of the reaction (TLC monitoring), the reaction mixture was cooled to 0° C., added water (50 ml) and extracted with ethyl acetate (3×50 ml). The combined organics was washed with saturated NaHCO3 solution, dried over Na2SO4, filtered and concentrated under vacuum to get the desired product (0.043 g, 68%).

後処理

  1. customthe resulting reaction mixture
  2. customAfter the completion of the reaction (TLC monitoring)
  3. temperaturethe reaction mixture was cooled to 0° C.
  4. extractionextracted with ethyl acetate (3×50 ml)
  5. washThe combined organics was washed with saturated NaHCO3 solution
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum

出典と根拠

ORDレコード
ord-33aa0356b7c5406e8ec4fe009113d37b
出典データセット
uspto-grants-2013_07
特許番号
US08492414B2

反応ノート

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