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

HRID 129957노트

반응식

HRID 129957 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 21801Titanium tetrabutoxide촉매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-3f169b14897446e38abb306a55f5528b
출처 데이터셋
uspto-grants-1995_11
특허 번호
US05470980

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