Hydrogen Bromide → 2-Bromo-5-(trifluoromethyl)-1,3,4-thiadiazole

HRID 917978ノート

反応式

HRID 917978 の反応式
N([O-])=O.[Na+].N[C:6]1[S:7][C:8]([C:11]([F:14])([F:13])[F:12])=[N:9][N:10]=1.[OH-].[Na+].S(=O)(O)[O-].[Na+].[BrH:22]>[Cu]>[Br:22][C:6]1[S:7][C:8]([C:11]([F:14])([F:13])[F:12])=[N:9][N:10]=1

参加物

7

反応物 5

HCID 260Hydrogen BromideHCID 14798Sodium HydroxideHCID 826341,3,4-Thiadiazol-2-amine, 5-(trifluoromethyl)-HCID 23665763Sodium BisulfiteHCID 23668193Sodium Nitrite

生成物 1

HCID 128746852-Bromo-5-(trifluoromethyl)-1,3,4-thiadiazole

試薬・触媒・溶媒 1

HCID 23978Copper触媒

実験手順

To a rapidly stirred suspension of copper bronze (6.1 g.) in 48% HBr (975 ml.) was added over a 1 hour period and cooling to -15° a mixture of NaNO2 (195 g., 2.83 mol.) and 2-amino-5-trifluoromethyl-1,3,4-thiadiazole (103 g., 0.61 mol.) [I. Lalezari and N. Sharghi, J. Hetero. Chem. 3:336 (1966)]. The resultant mixture was stirred for 0.75 hour with ice bath cooling and for 1.5 hour without cooling. The mixture was adjusted to pH 8 using 50% NaOH and maintaining the temperature below 20°. Saturated sodium bisulfite was added until a negative starch-iodide test was obtained. The mixture was made strongly acidic with HCL and extracted with petroleum ether. The extracts were washed with water, dried (MgSO4) and evaporated to the product. Distillation gave 2-bromo-5-trifluoromethyl-1,3,4-thiadiazole; b.p 56°-57°/11 mm.

後処理

  1. additionwas added over a 1 hour period
  2. temperaturecooling to -15°
  3. temperaturecooling and for 1.5 hour
  4. temperaturewithout cooling
  5. temperaturemaintaining the temperature below 20°
  6. customwas obtained
  7. extractionextracted with petroleum ether
  8. washThe extracts were washed with water
  9. dry with materialdried (MgSO4)
  10. customevaporated to the product
  11. distillationDistillation

出典と根拠

ORDレコード
ord-d3384256036f4e389ecb6c026a676236
出典データセット
uspto-grants-1976_07
特許番号
US03968226

反応ノート

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