Hydrogen Bromide → 2-Bromo-5-tert-butyl-1,3,4-thiadiazole

HRID 1253513ノート

反応式

HRID 1253513 の反応式
[C:1]([C:5]1[S:9][C:8](N)=[N:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].[BrH:11].N([O-])=O.[Na+]>C(O)(=O)C.O>[Br:11][C:8]1[S:9][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[N:6][N:7]=1

参加物

6

反応物 3

HCID 260Hydrogen BromideHCID 170170ButhidazolamineHCID 23668193Sodium Nitrite

生成物 1

HCID 204065272-Bromo-5-tert-butyl-1,3,4-thiadiazole

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 962Water溶媒

反応条件

温度
65 °C

実験手順

To a solution of crude 5-tert-butyl-1,3,4-thiadiazol-2-amine (120.8 g) in glacial acetic acid (800 ml) was added aqueous hydrobromic acid (≧40%, 218 ml) at room temperature. The resulting solution was heated to 65° C., and a solution of sodium nitrite (167 g, 2.42 mol) in water (300 ml) was added dropwise such that the internal temperature was maintained at 65˜75° C. After addition was complete, the resulting yellow solution was cooled to room temperature, poured into ice and then extracted with ethyl acetate. The combined organic layer was washed with saturated aqueous sodium carbonate solution until the pH was neutral, dried over magnesium sulfate, filtered and concentrated. The resulting oil was purified via flash column chromatography (ethyl acetate/petroleum ether) to obtain 2-bromo-5-tert-butyl-1,3,4-thiadiazole.

後処理

  1. temperaturewas maintained at 65˜75° C
  2. additionAfter addition
  3. temperaturethe resulting yellow solution was cooled to room temperature
  4. additionpoured into ice
  5. extractionextracted with ethyl acetate
  6. washThe combined organic layer was washed with saturated aqueous sodium carbonate solution until the pH
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe resulting oil was purified via flash column chromatography (ethyl acetate/petroleum ether)

出典と根拠

ORDレコード
ord-c799a20b45474747a09e71fa4309cb70
出典データセット
uspto-grants-2013_06
特許番号
US08455477B2

反応ノート

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