Methanol → 1,2,3-Benzothiadiazol-7-ylmethanol

HRID 257139

反応式

HRID 257139 の反応式
C([C:4]1[C:9]2[N:10]=[N:11][S:12][C:8]=2[CH:7]=[CH:6][CH:5]=1)(O)=O.B(OCC)(OCC)[O:14][CH2:15]C.CO>O1CCCC1>[OH:14][CH2:15][C:7]1[C:8]2[S:12][N:11]=[N:10][C:9]=2[CH:4]=[CH:5][CH:6]=1

参加物

5

反応物 3

HCID 887MethanolHCID 9009Triethyl borateHCID 200964341,2,3-Benzothiadiazole-4-carboxylic acid

生成物 1

HCID 200964331,2,3-Benzothiadiazol-7-ylmethanol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a suspension of 54 g of carboxybenzo-1,2,3-thiadiazole in 420 ml of tetrahydrofuran there are added dropwise under a nitrogen atmosphere with stirring at room temperature 110 ml of triethyl borate, the mixture is stirred for a further hour and subsequently treated dropwise with 45.6 ml of boranedimethyl sulfide complex in 60 ml of tetrahydrofuran, with gentle cooling, during which process gas is evolved vigorously. The mixture is stirred overnight and allowed to stand at room temperature and then cooled down to 5°-10° C. and treated dropwise with 200 ml of methanol with stirring and vigorous cooling, during which process gas is again evolved vigorously. The mixture is subsequently evaporated in vacuo, a further 300 ml of methanol are added, and the mixture is re-evaporated. The residue is purified on silica gel (solvent: ethyl acetate/hexane), and the product obtained is recrystallised from ethyl acetate/hexane. The title compound obtained melts at 79°-81° C.

後処理

  1. additionthere are added dropwise under a nitrogen atmosphere
  2. stirringThe mixture is stirred overnight
  3. customto stand at room temperature
  4. temperaturecooled down to 5°-10° C.
  5. stirringwith stirring
  6. customThe mixture is subsequently evaporated in vacuo
  7. additiona further 300 ml of methanol are added
  8. customthe mixture is re-evaporated
  9. customThe residue is purified on silica gel (solvent: ethyl acetate/hexane)
  10. customthe product obtained
  11. customis recrystallised from ethyl acetate/hexane

出典と根拠

ORDレコード
ord-478fe1fbbb92418783aff56d598578e6
出典データセット
uspto-grants-1993_11
特許番号
US05260423

関連ノート

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