Triethylamine → 2,2-Dimethyl-3-(1',1',2',2'-tetrachloroethylthio)-1,3-benzoxazin-4-one

HRID 259226

반응식

HRID 259226 반응식
[CH3:1][C:2]1([CH3:13])[NH:7][C:6](=[O:8])[C:5]2[CH:9]=[CH:10][CH:11]=[CH:12][C:4]=2[O:3]1.[Cl:14][C:15]([Cl:21])([S:19]Cl)[CH:16]([Cl:18])[Cl:17].C(N(CC)CC)C>ClCCl>[CH3:1][C:2]1([CH3:13])[N:7]([S:19][C:15]([Cl:21])([Cl:14])[CH:16]([Cl:18])[Cl:17])[C:6](=[O:8])[C:5]2[CH:9]=[CH:10][CH:11]=[CH:12][C:4]=2[O:3]1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 144531,1,2,2-Tetrachloroethylsulfenyl chlorideHCID 7174282,2-dimethyl-3,4-dihydro-2H-1,3-benzoxazin-4-one

생성물 1

HCID 214236532,2-Dimethyl-3-(1',1',2',2'-tetrachloroethylthio)-1,3-benzoxazin-4-one수율 15.9%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
0 °C

실험 절차

A 250-ml flask equipped with condenser, stirrer and thermometer and immersed in an ice bath was charged with 150 ml of dichloromethane, 8.3 g (0.047 mol) of 2,2-dimethyl-1,3-benzoxazin-4-one and 10.9 g (0.047 mol) of 1,1,2,2-tetrachloroethylsulfenyl chloride. Then 4.75 g (0.047 mol) of triethylamine dissolved in 10 ml of dichloromethane was added dropwise over a period of 15 minutes. The resulting solution was stirred at 0° C. for 45 more minutes. The crude reaction mixture was washed three times with equal quantities of water. The organic phase was dried and then stripped of solvent. The resulting residue was washed with 200 ml of hexane and filtered. The dried filter cake, 5.1 g, was unreacted 2,2-dimethyl-1,3-benzoxazin-4-one. The filtrate was stripped of hexane and the resulting residue was chromatographed through 300 g of silica gel using 1 liter of hexane, 1 liter of 3% ether-hexane and 3 liters of 5% ether-hexane to give 2.8 g of 2,2-dimethyl-3-(1',1',2',2'-tetrachloroethylthio)-1,3-benzoxazin-4-one. Analysis, calculated for C12H11Cl4NO2S: %C, 37.81; %S, 8.55. Found: %Cl, 40.0; %S, 8.8. NMR spectra confirmed the assigned structure. The infrared spectra had strong adsorption at 1785, 1600, 1460, 1300, 1240 and 740 cm-1. These spectra also had many distinct, medium-strength adsorption bands in the 800-1700 cm-1 region.

후처리

  1. customA 250-ml flask equipped with condenser, stirrer
  2. customthermometer and immersed in an ice bath
  3. additionwas added dropwise over a period of 15 minutes
  4. customThe crude reaction mixture
  5. washwas washed three times with equal quantities of water
  6. customThe organic phase was dried
  7. washThe resulting residue was washed with 200 ml of hexane
  8. filtrationfiltered
  9. filtrationThe dried filter cake, 5.1 g
  10. customthe resulting residue was chromatographed through 300 g of silica gel using 1 liter of hexane, 1 liter of 3% ether-hexane and 3 liters of 5% ether-hexane

출처 및 근거

ORD 기록
ord-444e340b7a9046a7a89cad71136e45b3
출처 데이터셋
uspto-grants-1977_07
특허 번호
US04036960

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