Benzonitrile → 2-Aminobenzothiazole-6-carbonitrile

HRID 9102

反応式

HRID 9102 の反応式
[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

参加物

7

反応物 4

HCID 7505BenzonitrileHCID 133964-AminobenzonitrileHCID 24408BromineHCID 516872Potassium thiocyanate

生成物 1

HCID 43271392-Aminobenzothiazole-6-carbonitrile収率 67.4%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒2 回HCID 962Water溶媒

反応条件

温度
16 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-5037c9c33a5a49e9b0b5c20797e25f9c
出典データセット
uspto-grants-2006_08
特許番号
US07091227B2

関連ノート

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