Benzothiazole, 2,5-dimethyl- → 4-Bromo-2,5-dimethyl-1,3-benzothiazole

HRID 1192463노트

반응식

HRID 1192463 반응식
[CH3:1][C:2]1[S:3][C:4]2[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][C:5]=2[N:6]=1.[Br:12]Br>C(Cl)(Cl)Cl>[Br:12][C:7]1[C:5]2[N:6]=[C:2]([CH3:1])[S:3][C:4]=2[CH:10]=[CH:9][C:8]=1[CH3:11]

참가 물질

4

반응물 2

HCID 7227Benzothiazole, 2,5-dimethyl-HCID 24408Bromine

생성물 1

HCID 672576564-Bromo-2,5-dimethyl-1,3-benzothiazole

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

A mixture of 2,5-dimethyl-1,3-benzothiazole (10.00 g, 61.26 mmol, Aldrich) and bromine (6.94 mL, 134.8 mmol) in chloroform (200 mL) was heated at reflux overnight. After cooling to room temperature, the mixture was washed with 1 N NaOH, followed by saturated sodium thiosulfate and brine, then dried over sodium sulfate and evaporated to dryness. The residue was purified on silica gel, eluting with 0 to 50% EtOAc in hexane. The first peak had a retention time of 2.51 minutes, LCMS calculated for C9H9BrNS(M+H)+: m/z=242.0; found: 241.9. 1H NMR shown to be the desired product B (980 mg, 6.61%). 1H NMR (CDCl3, 400 MHz) 7.63 (1H, d, J=8.4 Hz), 7.22 (1H, d, J=8.4 Hz), 2.87 (3H, s), 2.55 (3H, s) ppm. The second peak had a retention time of 2.758 minutes, LCMS (M+H)+m/z=241.9; found: 242. 1H NMR showed no coupling for the two phenyl hydrogens confirming the 6-bromo isomer.

후처리

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. washthe mixture was washed with 1 N NaOH
  4. dry with materialdried over sodium sulfate
  5. customevaporated to dryness
  6. customThe residue was purified on silica gel
  7. washeluting with 0 to 50% EtOAc in hexane

출처 및 근거

ORD 기록
ord-0ad568de7f144c1bad7775d5328fcff0
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08680108B2

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