Dimethylformamide → 5-Benzothiazolecarbonitrile

HRID 1507544노트

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HRID 1507544 반응식
Br[C:2]1[CH:3]=[CH:4][C:5]2[S:9][CH:8]=[N:7][C:6]=2[CH:10]=1.[CH3:11][N:12](C)C=O>[C-]#N.[Zn+2].[C-]#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[S:9]1[C:5]2[CH:4]=[CH:3][C:2]([C:11]#[N:12])=[CH:10][C:6]=2[N:7]=[CH:8]1

참가 물질

5

반응물 2

HCID 6228DimethylformamideHCID 36101555-Bromobenzothiazole

생성물 1

HCID 107021045-Benzothiazolecarbonitrile

시약·촉매·용매 2

HCID 11186Zinc cyanide (Zn(CN)2)촉매HCID 178418397HCID 178418397, 화합물촉매

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온도
80 °C

실험 절차

Into a mixture of 5-bromo-1,3-benzothiazole (300 mg, 1.40 mmol, 1.00 equiv) and zinc cyanide (131.6 mg, 0.80 equiv) in N,N-dimethylformamide (6.0 mL) was added Pd(PPh3)4 (80.9 mg, 0.07 mmol, 0.05 equiv) and nitrogen was bubbled for 5 min. The resulting mixture was heated overnight at 80° C., quenched by water (15.0 mL), and extracted with ethyl acetate (3×15 mL). The combined organic layers were washed with brine (2×15 mL) and dried over Na2SO4. After filtered and concentrated under reduced pressure, the residue was purified by flash chromatography on silica gel, eluting with a mixture of 5-10% ethyl acetate in petroleum ether to afford the title compound as a light yellow solid. MS m/z [M+H]+ (ESI): 161.

후처리

  1. customwas bubbled for 5 min
  2. customquenched by water (15.0 mL)
  3. extractionextracted with ethyl acetate (3×15 mL)
  4. washThe combined organic layers were washed with brine (2×15 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationAfter filtered
  7. concentrationconcentrated under reduced pressure
  8. customthe residue was purified by flash chromatography on silica gel
  9. washeluting with a mixture of 5-10% ethyl acetate in petroleum ether

출처 및 근거

ORD 기록
ord-4c90cfa129fe4e0b9538ebb17075bc13
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09221809B2

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