Diethyl azodicarboxylate → HCID 14989389、化合物

HRID 981659ノート

反応式

HRID 981659 の反応式
[Cl:1][C:2]1[N:7]=[N:6][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][CH2:16]O)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[SH:18][C:19]1[CH:29]=[CH:28][C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:21][CH:20]=1.CCOC(/N=N/C(OCC)=O)=O>O1CCCC1>[Cl:1][C:2]1[N:7]=[N:6][C:5]([N:8]2[CH2:9][CH2:10][CH:11]([CH2:14][CH2:15][CH2:16][S:18][C:19]3[CH:20]=[CH:21][C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:28][CH:29]=3)[CH2:12][CH2:13]2)=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 5462977Diethyl azodicarboxylateHCID 10845149ethyl 4-mercaptobenzoateHCID 14989224HCID 14989224、化合物

生成物 1

HCID 14989389HCID 14989389、化合物収率 13.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a stirred solution of 5.6 parts of 1-(6-chloro-3-pyridazinyl)-4-piperidinepropanol, 4.2 parts of ethyl 4-mercaptobenzoate and 6 parts of triphenylposphine in 135 parts of tetrahydrofuran was added dropwise a solution of 4 parts of diethyl diazenedicarboxylate in 45 parts of tetrahydrofuran at 20° C. Upon complete addition, stirring was continued overnight at this temperature. The reaction mixture was evaporated and the residue was taken up in water. The product was ectracted with dichloromethane. The extract was dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (99:1 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from 2,2'-oxybispropane. The product was filtered off and dried, yielding 1.3 parts (13.5%) of ethyl 4-[[3-[1-(6-chloro-3-pyridazinyl)-4-piperidinyl]propyl]thio]benzoate; mp. 96.3° C. (comp. 164).

後処理

  1. additionUpon complete addition
  2. customThe reaction mixture was evaporated
  3. customThe extract was dried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by column chromatography over silica gel using
  7. additiona mixture of trichloromethane and methanol (99:1 by volume) as eluent
  8. customThe pure fractions were collected
  9. customthe eluent was evaporated
  10. customThe residue was crystallized from 2,2'-oxybispropane
  11. filtrationThe product was filtered off
  12. customdried

出典と根拠

ORDレコード
ord-635f8a4045eb4a5e960df0a16643ca88
出典データセット
uspto-grants-1991_02
特許番号
US04992433

反応ノート

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