4,7-Dibromo-2,1,3-benzothiadiazole → 3,6-Dibromobenzene-1,2-diamine

HRID 43218

反応式

HRID 43218 の反応式
[BH4-].[Na+].[Br:3][C:4]1[C:9]2=[N:10]S[N:12]=[C:8]2[C:7]([Br:13])=[CH:6][CH:5]=1>CCO>[Br:3][C:4]1[CH:5]=[CH:6][C:7]([Br:13])=[C:8]([NH2:12])[C:9]=1[NH2:10]

参加物

4

反応物 2

HCID 6263614,7-Dibromo-2,1,3-benzothiadiazoleHCID 4311764Sodium borohydride

生成物 1

HCID 118215323,6-Dibromobenzene-1,2-diamine収率 66.4%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
30 °C

実験手順

NaBH4 (26 g, 680 mmol, 10 equiv) was added portionwise (2 h) to a vigorously stirred suspension of 4,7-dibromo-benzo[1,2,5]thiadiazole (Step 179.7) (20 g, 68.0 mmol) in EtOH (400 mL), under a nitrogen atmosphere and keeping the internal temperature below 15° C. The reaction mixture was allowed to warm to 30° C., stirred for 1 h, cooled to 5° C., quenched by addition of H2O (50 mL), and concentrated. The residue was diluted with Et2O/H2O. The resulting suspension was filtered and the filtrate extracted with Et2O. The organic phase was washed with H2O and brine, dried (Na2SO4), filtered and concentrated. The residue was triturated in hexane to provide 12 g of the title compound as a white solid: ESI-MS: 263/265/267 [M−H]−; tR=4.20 min (System 1).

後処理

  1. customthe internal temperature below 15° C
  2. temperaturecooled to 5° C.
  3. customquenched by addition of H2O (50 mL)
  4. concentrationconcentrated
  5. additionThe residue was diluted with Et2O/H2O
  6. filtrationThe resulting suspension was filtered
  7. extractionthe filtrate extracted with Et2O
  8. washThe organic phase was washed with H2O and brine
  9. dry with materialdried (Na2SO4)
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customThe residue was triturated in hexane

出典と根拠

ORDレコード
ord-d1709645b07944c4b9477092e0b7297b
出典データセット
uspto-grants-2013_09
特許番号
US08536175B2

関連ノート

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