Hydrochloric Acid → Diethyl 2-(benzo-1,2,3-thiadiazol-7-yl)malonate

HRID 6362

反応式

HRID 6362 の反応式
[Cl-].[Mg+2].[Cl-].[C:4]([O:12][CH2:13][CH3:14])(=[O:11])[CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7].[S:15]1[C:19]2[C:20](C(Cl)=O)=[CH:21][CH:22]=[CH:23][C:18]=2[N:17]=[N:16]1.Cl>C(#N)C.C(N(CC)CC)C>[S:15]1[C:19]2[C:20]([CH:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[C:4]([O:12][CH2:13][CH3:14])=[O:11])=[CH:21][CH:22]=[CH:23][C:18]=2[N:17]=[N:16]1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 7761Diethyl MalonateHCID 5360315Magnesium ChlorideHCID 183776071,2,3-Benzothiadiazole-7-carbonyl chloride

生成物 1

HCID 19793424Diethyl 2-(benzo-1,2,3-thiadiazol-7-yl)malonate収率 83.2%

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒2 回HCID 8471Triethylamine溶媒

反応条件

温度
0 °C

実験手順

4.8 g of magnesium chloride in 50 ml of acetonitrile are treated with 7.6 ml of diethyl malonate and 14 ml of triethylamine, with ice-cooling and stirring. The mixture is stirred for 20 minutes and then treated at 0°-5° C. with portions of a suspension of 9.6 g of benzo-1,2,3-thiadiazole-7-carboxylic acid chloride in 50 ml of acetonitrile, the temperature being maintained at between 5° C. and 15° C. The resulting beige suspension is stirred for a further hour in an ice-bath at 0° C. and subsequently overnight at room temperature. On the next day, it is cooled again to 0° C., brought to pH 4.5 using 15% hydrochloric acid, and extracted with ethyl acetate. The extracts are dried over sodium sulfate, filtered over silica gel and evaporated. This results in the title compound in a yield of 83.2% of theory and with a melting point of 72°-74° C.

後処理

  1. temperaturecooling
  2. stirringThe mixture is stirred for 20 minutes
  3. temperaturethe temperature being maintained at between 5° C. and 15° C
  4. stirringThe resulting beige suspension is stirred for a further hour in an ice-bath at 0° C. and subsequently overnight at room temperature
  5. extractionextracted with ethyl acetate
  6. dry with materialThe extracts are dried over sodium sulfate
  7. filtrationfiltered over silica gel
  8. customevaporated

出典と根拠

ORDレコード
ord-ac19de6fdddf43cb807f1b8ce12dad02
出典データセット
uspto-grants-1993_09
特許番号
US05248683

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