Methyl hydrazidodicarboxylate → Bis(1-methoxy-2,2,6,6-tetramethylpiperidin-4-yl) Hydrazine-1,2-dicarboxylate

HRID 129957ノート

反応式

HRID 129957 の反応式
[CH3:1][O:2][N:3]1[C:8]([CH3:10])([CH3:9])[CH2:7][CH:6]([OH:11])[CH2:5][C:4]1([CH3:13])[CH3:12].[NH:14]([C:20]([O:22]C)=O)[NH:15][C:16]([O:18][CH3:19])=[O:17]>CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-].[Ti+4]>[NH:15]([C:16]([O:18][CH:19]1[CH2:10][C:8]([CH3:9])([CH3:7])[N:3]([O:2][CH3:1])[C:4]([CH3:13])([CH3:12])[CH2:5]1)=[O:17])[NH:14][C:20]([O:11][CH:6]1[CH2:7][C:8]([CH3:9])([CH3:10])[N:3]([O:2][CH3:1])[C:4]([CH3:13])([CH3:12])[CH2:5]1)=[O:22]

参加物

4

反応物 2

HCID 265934Methyl hydrazidodicarboxylateHCID 109977701-Methoxy-2,2,6,6-tetramethyl-piperidin-4-ol

生成物 1

HCID 54536773Bis(1-methoxy-2,2,6,6-tetramethylpiperidin-4-yl) Hydrazine-1,2-dicarboxylate収率 64%

試薬・触媒・溶媒 1

HCID 21801Titanium tetrabutoxide触媒

実験手順

To a mixture of 15.8 g of 1-methoxy-2,2,6,6-tetramethylpiperidin-4-ol and 5.9 g of dimethyl hydrazine-1,2-dicarboxylate is added 1.4 g of tetrabutyl titanate at room temperature. The mixture is heated at 135°-145° C. for 12 hours and methanol is collected in a Dean-Stark trap. The reaction mixture is partitioned between toluene and water. The organic phase is then washed with water, brine, dried over anhydrous sodium sulfate and evaporated to leave 19.1 g of the crude desired product. Recrystallization of the crude product from acetonitrile affords 11.7 g of the title compound as an off-white solid; mp 147°-149° C.

後処理

  1. temperatureThe mixture is heated at 135°-145° C. for 12 hours
  2. custommethanol is collected in a Dean-Stark trap
  3. customThe reaction mixture is partitioned between toluene and water
  4. washThe organic phase is then washed with water, brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated
  7. customto leave 19.1 g of the crude desired product
  8. customRecrystallization of the crude product from acetonitrile

出典と根拠

ORDレコード
ord-3f169b14897446e38abb306a55f5528b
出典データセット
uspto-grants-1995_11
特許番号
US05470980

反応ノート

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