Phosgene → 1-Chlorocarbonyl-3-[3-(trifluoromethyl)phenoxy]azetidine

HRID 974549

반응식

HRID 974549 반응식
[C:1]([Cl:4])(Cl)=[O:2].C(=O)([O-])[O-].[K+].[K+].C1(C(C2C=CC=CC=2)[N:18]2[CH2:21][CH:20]([O:22][C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[CH:24]=3)[CH2:19]2)C=CC=CC=1>C(Cl)Cl>[F:32][C:29]([F:30])([F:31])[C:25]1[CH:24]=[C:23]([CH:28]=[CH:27][CH:26]=1)[O:22][CH:20]1[CH2:21][N:18]([C:1]([Cl:4])=[O:2])[CH2:19]1

참가 물질

5

반응물 3

HCID 6371PhosgeneHCID 11430Potassium CarbonateHCID 117286941-Benzhydryl-3-[3-(trifluoromethyl)phenoxy]azetidine

생성물 1

HCID 197996061-Chlorocarbonyl-3-[3-(trifluoromethyl)phenoxy]azetidine수율 62%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

A solution of 35.6 g (0.36 mole) of phosgene in 200 ml of methylene chloride at 5° C. was stirred with 50 g (0.36 mole) of potassium carbonate for 1 hr. To the mixture was added dropwise 115 g (0.3 mole) of 1-diphenylmethyl-3-[-3-(trifluoromethyl)phenoxy]azetidine in 400 ml of methylene chloride. After stirring for 18 hr, the reaction mixture was filtered and the filtrate was washed with water, dried over magnesium sulfate and concentrated on a rotary evaporator to a viscous oil residue, 133.2 g. Trituration of the residue with hexane gave a solid which was recrystallized from cold hexane to yield 52 g (62%) of white crystals, m.p. 72.5°-74° C.

후처리

  1. filtrationthe reaction mixture was filtered
  2. washthe filtrate was washed with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated on a rotary evaporator to a viscous oil residue, 133.2 g
  5. customTrituration of the residue with hexane gave a solid which
  6. customwas recrystallized from cold hexane

출처 및 근거

ORD 기록
ord-af588826d4cf4c0aaa532385c2c04d5a
출처 데이터셋
uspto-grants-1991_11
특허 번호
US05068231

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