Diethyl Ether → N-Acryloyl-D-glucamine

HRID 374405

반응식

HRID 374405 반응식
[NH2:1][CH2:2][C@@H:3]([C@H:5]([C@@H:7]([C@@H:9]([CH2:11][OH:12])[OH:10])[OH:8])[OH:6])[OH:4].N([O-])=O.[Na+].[C:17](Cl)(=[O:20])[CH:18]=[CH2:19].CCOCC>C([O-])([O-])=O.[K+].[K+]>[C:17]([NH:1][CH2:2][C@@H:3]([C@H:5]([C@@H:7]([C@@H:9]([CH2:11][OH:12])[OH:10])[OH:8])[OH:6])[OH:4])(=[O:20])[CH:18]=[CH2:19]

참가 물질

6

반응물 4

HCID 3283Diethyl Ether2회HCID 13140Acryloyl chlorideHCID 452501GlucamineHCID 23668193Sodium Nitrite

생성물 1

HCID 18639241N-Acryloyl-D-glucamine

시약·촉매·용매 1

HCID 11430Potassium Carbonate용매

실험 절차

1-Amino-1-deoxy-D-glucitol (0.16 mol; 29 g) and 0.2 g NaNO2 were dissolved under a nitrogen atmosphere at 0° C. in 100 ml of a 0.3M K2CO3 solution. Acryloyl chloride (0.32 mol; 28.96 g) was added under vigorous stirring. The reaction was carried out similar to the synthesis of 1. After addition of ether, white crystals and a yellow oil were formed. The crystals were separated and gave the product, while the oil was discharged. Stepwise addition of 2 l of ether to the mother liquid and storing it in the refrigerator gave more of the desired product. For further purification the crystals were recrystallized twice from water/ethanol/ether. Yield: 22.2 g (59%), m.p.: 125° C.

후처리

  1. customThe reaction was carried out similar to the synthesis of 1
  2. customa yellow oil were formed
  3. customThe crystals were separated
  4. customgave the product

출처 및 근거

ORD 기록
ord-b5de157fa22144f68f6d24e74e96c36b
출처 데이터셋
uspto-grants-1996_01
특허 번호
US05480790

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