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

HRID 43048

반응식

HRID 43048 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

HCID 118215323,6-Dibromobenzene-1,2-diamine수율 66.4%

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
30 °C

실험 절차

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 1.7) (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: 262.9/264.9/266.9 [M−H]−; tR=4.20 min (System 1).

후처리

  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

출처 및 근거

ORD 기록
ord-52494ee422464adcbc510367089c2322
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08536175B2

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