Methylamine → 3-(4-Fluorophenoxy)-N-methyl-1-azetidinecarboxamide

HRID 974603

반응식

HRID 974603 반응식
[F:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][CH:7]2[CH2:10][N:9]([C:11](Cl)=[O:12])[CH2:8]2)=[CH:4][CH:3]=1.[CH3:16][NH2:17]>O1CCCC1.C(Cl)Cl>[F:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][CH:7]2[CH2:10][N:9]([C:11]([NH:17][CH3:16])=[O:12])[CH2:8]2)=[CH:4][CH:3]=1

참가 물질

5

반응물 2

HCID 6329MethylamineHCID 150533673-(4-Fluorophenoxy)-1-azetidinecarbonyl chloride

생성물 1

HCID 150534373-(4-Fluorophenoxy)-N-methyl-1-azetidinecarboxamide수율 129.3%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 4.6 g (0.02 mole) of 3-(4-fluorophenoxy)-1-azetidinecarbonyl chloride in 15 ml of tetrahydrofuran was stirred while 6.2 g (0.08 mole) of 40% aqueous methylamine was added. The reaction mixture was exothermic and was allowed to cool to ambient temperature while stirring for 18 hr. The reaction mixture was diluted with 200 ml of ice water and the oil droplets which separated quickly crystallized. Filtration yielded 6.6 g of crude product. The solid was dissolved in 100 ml of methylene chloride, treated with 15 g of silica gel and stirred for 2 hr. The silica gel was removed by filtration and washed wit 200 ml of 50/50 ethyl acetatemethylene chloride. The combined filtrates were concentrated on a rotary evaporator, yielding 5.8 g of solid residue. The solid was recrystallized by dissolving in 22 ml of acetone and adding 88 ml of isopropyl ether. The volume was reduced to 40 ml by boiling under nitrogen atmosphere and upon cooling the product crystallized. Filtration yielded 2.95 (66.7%) of white crystals, m.p. 140°-142° C.

후처리

  1. additionwas added
  2. customthe oil droplets which separated quickly
  3. customcrystallized
  4. filtrationFiltration
  5. customyielded 6.6 g of crude product
  6. additiontreated with 15 g of silica gel
  7. stirringstirred for 2 hr
  8. customThe silica gel was removed by filtration
  9. washwashed wit 200 ml of 50/50 ethyl acetatemethylene chloride
  10. concentrationThe combined filtrates were concentrated on a rotary evaporator

출처 및 근거

ORD 기록
ord-f75f0d7ea04c43aaa84e1e4db2741c27
출처 데이터셋
uspto-grants-1991_11
특허 번호
US05068231

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