Dimethyl Sulfoxide → 6-cyano-3,4-dihydro-2,2-dimethyl-4(2-oxocyclopentyl)-2H-1,4-benzoxazine

HRID 37120노트

반응식

HRID 37120 반응식
CS(C)=O.[C:5]([C:7]1[CH:8]=[CH:9][C:10]2[O:15][C:14]([CH3:17])([CH3:16])[CH2:13][N:12]([CH:18]3[CH2:22][CH2:21][CH2:20][CH:19]3[OH:23])[C:11]=2[CH:24]=1)#[N:6].C(N(CC)CC)C>C(Cl)Cl.C(Cl)(=O)C(Cl)=O.O>[C:5]([C:7]1[CH:8]=[CH:9][C:10]2[O:15][C:14]([CH3:17])([CH3:16])[CH2:13][N:12]([CH:18]3[CH2:22][CH2:21][CH2:20][C:19]3=[O:23])[C:11]=2[CH:24]=1)#[N:6]

참가 물질

7

반응물 3

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 199345646-cyano-3,4-dihydro-2,2-dimethyl-4-(2-hydroxycyclopentan-1-yl)-2H-1,4-benzoxazine

생성물 1

HCID 106834746-cyano-3,4-dihydro-2,2-dimethyl-4(2-oxocyclopentyl)-2H-1,4-benzoxazine수율 52.2%

시약·촉매·용매 3

HCID 962Water용매HCID 6344Dichloromethane용매3회HCID 65578Oxalyl chloride용매

실험 절차

In 5 ml of methylene chloride was dissolved 0.2 ml of oxalyl chloride and at a constant temperature between -50° C. and -60° C., a solution prepared by dissolving 0.34 ml of dimethyl sulfoxide in 1 ml of methylene chloride was added dropwise. The mixture was stirred for 2 minutes, after which a solution of 0.54 g of 6-cyano-3,4-dihydro-2,2-dimethyl-4-(2-hydroxycyclopentan-1-yl)-2H-1,4-benzoxazine in 2 ml of methylene chloride was added dropwise. The mixture was further stirred for 15 minutes and 0.7 ml of triethylamine was added. The mixture was stirred for an additional 5 minutes, after which it was allowed to return to room temperature. The reaction mixture was diluted with 10 ml of water and extracted with methylene chloride. The extract was washed with aqueous sodium chloride solution and dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. The residue was recovered by filtration, washed with ethanol and recrystallized from ethyl acetate to give 0.28 g of 6-cyano-3,4-dihydro-2,2-dimethyl-4(2-oxocyclopentyl)-2H-1,4-benzoxazine.

후처리

  1. customat a constant temperature between -50° C. and -60° C., a solution prepared
  2. additionwas added dropwise
  3. stirringThe mixture was further stirred for 15 minutes
  4. stirringThe mixture was stirred for an additional 5 minutes
  5. customto return to room temperature
  6. extractionextracted with methylene chloride
  7. washThe extract was washed with aqueous sodium chloride solution
  8. dry with materialdried over anhydrous magnesium sulfate
  9. distillationthe solvent was distilled off under reduced pressure
  10. filtrationThe residue was recovered by filtration
  11. washwashed with ethanol
  12. customrecrystallized from ethyl acetate

출처 및 근거

ORD 기록
ord-6ae0e0ccde2c4fd48a16193d6a52ab20
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05420126

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