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

HRID 615815ノート

反応式

HRID 615815 の反応式
[BrH:1].N[C:3]1[S:4][C:5]([C:8]([CH3:11])([CH3:10])[CH3:9])=[N:6][N:7]=1.N([O-])=O.[Na+]>C(O)(=O)C.O>[Br:1][C:3]1[S:4][C:5]([C:8]([CH3:11])([CH3:10])[CH3:9])=[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収率 78%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 962Water溶媒2 回

反応条件

温度
65 °C

実験手順

48% Aqueous hydrobromic acid (67.5 ml) was added to a solution of 2-amino-5-t-butyl-1,3,4-thiadiazole (43 g) in glacial acetic acid (300 ml) the mixture was warmed to 65° C. and a solution of sodium nitrite (56 g) in water (80 ml) was added dropwise with stirring over 60 minutes at 65°-75° C. The mixture was cooled to 20° C. and was poured into water. The organic layer was extracted into ether (2×300 ml) and the extracts were combined, washed with sodium bicarbonate solution until neutral and dried over magnesium sulphate. The drying agent was filtered off and the solvent was evaporated to give a yellow oil which was distilled under reduced pressure to give 2-bromo-5-t-butyl-1,3,4-thiadiazole (47 g, 78%) as a colourless liquid, bp 134°-136° C. at 23 mm Hg.

後処理

  1. temperatureThe mixture was cooled to 20° C.
  2. extractionThe organic layer was extracted into ether (2×300 ml)
  3. washwashed with sodium bicarbonate solution until neutral and
  4. dry with materialdried over magnesium sulphate
  5. filtrationThe drying agent was filtered off
  6. customthe solvent was evaporated
  7. customto give a yellow oil which
  8. distillationwas distilled under reduced pressure

出典と根拠

ORDレコード
ord-e024c29c45a747289667d74530b9d874
出典データセット
uspto-grants-1985_02
特許番号
US04501605

反応ノート

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