Isobutylene → 1-Tertiarybutyl-3,3-dinitroazetidine hydrochloride

HRID 1608673노트

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HRID 1608673 반응식
[C:1]([N:5]1[CH2:8][C:7]([N+:12]([O-:14])=[O:13])([N+:9]([O-:11])=[O:10])[CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[Cl:15]C(OCC1C=CC=CC=1)=O.CC(=C)C>C(Cl)(Cl)Cl>[ClH:15].[C:1]([N:5]1[CH2:6][C:7]([N+:12]([O-:14])=[O:13])([N+:9]([O-:11])=[O:10])[CH2:8]1)([CH3:4])([CH3:2])[CH3:3]

참가 물질

5

반응물 3

HCID 8255IsobutyleneHCID 10387Benzyl chloroformateHCID 10954639Tert-butyl-3,3-dinitroazetidine

생성물 1

HCID 200870521-Tertiarybutyl-3,3-dinitroazetidine hydrochloride수율 49.5%

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

To 1-tertiary-butyl-3,3-dinitroazetidine (20 g, 0.099 mole) in 25 milliliters (ml) of chloroform was added benzyl chloroformate (9.24 g, 0.054 mole). The mixture was stirred under reflux for 24 hours during which time isobutylene was generated and a white precipitate was formed. The mixture was allowed to cool and was the precipitate was separated by filtration. The filter cake was washed with methylene chloride, air dried and weighed to yield 6.4 g (27%) of 1-tertiary-butyl-3,3-dinitroazetidine hydrochloride. The filtrate was evaporated under vacuum to yield a yellow solid. This solid was taken up in warm toluene, the mixture filtered while hot, and the filtrate treated with hexanes to crystallize the product. The resultant product was collected by filtration and dried to give 7.3 g (26% yield) of pure 1-(benzyloxycarbonyl)-3,3-dinitroazetidine. The melting point of the product was 77.5°-78°. Later runs with longer reaction times between the 1-tertiary-butyl-3,3-dinitroazetidine and benzyl chloroformate in refluxing methylene chloride afforded higher yields.

후처리

  1. customa white precipitate was formed
  2. temperatureto cool
  3. customwas separated by filtration
  4. washThe filter cake was washed with methylene chloride, air
  5. customdried

출처 및 근거

ORD 기록
ord-c477b0c9a08d4073a8215e6c5f219a49
출처 데이터셋
uspto-grants-1995_03
특허 번호
US05395945

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