Pyridine → naphthalen-1-yl N-methyl-N-phenylsulfinothioylcarbamate

HRID 1154758

반응식

HRID 1154758 반응식
[CH3:1][NH:2][C:3](=[O:15])[O:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][CH:6]=1.N1C=CC=CC=1.[S:22](Cl)(Cl)=O.[C:26]1([SH:32])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>O1CCCC1>[CH3:1][N:2]([S:32]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[S:22])[C:3](=[O:15])[O:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][CH:6]=1

참가 물질

6

반응물 4

HCID 1049Pyridine2회HCID 6129CarbarylHCID 7969ThiophenolHCID 24386Thionyl Chloride

생성물 1

HCID 53471807naphthalen-1-yl N-methyl-N-phenylsulfinothioylcarbamate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 1-naphthyl methylcarbamate (4.0 g, 0.02 mol) in 20 ml dry tetrahydrofuran was added 1.9 g pyridine (0.024 mol) and 2.5 g thionyl chloride (0.021 mol). The mixture was stirred at room temperature for 6 hours. The reaction mixture was cooled in an ice-water bath and 1.9 g pyridine was added followed by 2.2 g benzenethiol (0.02 mol) added dropwise. Stirring was continued for an additional 1 hour and the mixture was worked up in the usual manner as previously described in Example I. A sample was purified by preparative thin-layer chromatography. Nmr spectrum of the pure product in chloroform-d-TMS showed the following absorptions: δ8.1-6.9 (m, 12H, aromatic protons), 3.2 (s, 3H, NCH3).

후처리

  1. temperatureThe reaction mixture was cooled in an ice-water bath
  2. additionadded dropwise
  3. stirringStirring
  4. waitwas continued for an additional 1 hour
  5. customA sample was purified by preparative thin-layer chromatography

출처 및 근거

ORD 기록
ord-488a3e79ecb34e62b251a6079f753d02
출처 데이터셋
uspto-grants-1981_11
특허 번호
US04298527

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