Benzonitrile → 2-Aminobenzothiazole-6-carbonitrile

HRID 9102

반응식

HRID 9102 반응식
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[S-:10][C:11]#[N:12].[K+].BrBr.C(#N)C1C=CC=CC=1>C(O)(=O)C.O>[NH2:12][C:11]1[S:10][C:3]2[CH:4]=[C:5]([C:6]#[N:7])[CH:8]=[CH:9][C:2]=2[N:1]=1

참가 물질

7

반응물 4

HCID 7505BenzonitrileHCID 133964-AminobenzonitrileHCID 24408BromineHCID 516872Potassium thiocyanate

생성물 1

HCID 43271392-Aminobenzothiazole-6-carbonitrile수율 67.4%

시약·촉매·용매 2

HCID 176Acetic Acid용매2회HCID 962Water용매

반응 조건

온도
16 °C

실험 절차

Two grams of 4-aminobenzonitrile was dissolved in about 40 mL acetic acid and the solution was cooled to about 16° C. About 3.3 g of potassium thiocyanate was added and the flask was equipped with an addition funnel. The addition funnel was charged with about 2.7 g bromine and about 5 mL acetic acid. This dark solution was then added to the benzonitrile solution in a dropwise fashion under good agitation and allowed to stir for about 16 hours. The slurry was then drowned into water and filtered. The presscake was washed well with water, reslurried in dilute aqueous alkali and filtered. Again the presscake was washed well with water. After drying in vacuo, about 2 grams of the title compound was isolated. 1H NMR 6.8 (d, 1H, J=8.7 Hz), 6.9 (br s, 2H), 7.6 (dd, 1H, J=2 Hz, J=8.7 Hz), 8.0 (d, 1H, J=2 Hz), LC/MS 2.34 min, 174 (M−H−), RP-HPLC RT 7.7 minutes.

후처리

  1. customthe flask was equipped with an addition funnel
  2. filtrationfiltered
  3. washThe presscake was washed well with water
  4. filtrationfiltered
  5. washAgain the presscake was washed well with water
  6. customAfter drying in vacuo

출처 및 근거

ORD 기록
ord-5037c9c33a5a49e9b0b5c20797e25f9c
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091227B2

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