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Pyridine → [4-(2,6-dichlorophenyl)-1,2,5-thiadiazol-3-yl] N-(2-cyanoethyl)-N-methyl-carbamate

HRID 617446
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HRID 617446 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[C:13]([OH:14])=[N:12][S:11][N:10]=1.[C:15](=[O:26])(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl.N1C=CC=CC=1.[C:33]([CH2:35][CH2:36][NH:37][CH3:38])#[N:34]>ClCCl.O>[CH3:38][N:37]([C:15]([O:14][C:13]1[C:9]([C:3]2[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][C:4]=2[Cl:8])=[N:10][S:11][N:12]=1)=[O:26])[CH2:36][CH2:35][C:33]#[N:34]
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참가 물질

7

반응물 4

HCID 1049PyridineHCID 69656Propanenitrile, 3-(methylamino)-HCID 94429TriphosgeneHCID 178519022HCID 178519022, 화합물

생성물 1

HCID 477329[4-(2,6-dichlorophenyl)-1,2,5-thiadiazol-3-yl] N-(2-cyanoethyl)-N-methyl-carbamate수율 290.8%

시약·촉매·용매 2

HCID 962
Water
용매
HCID 6344Dichloromethane용매

실험 절차

In 50 mL of dichloromethane, were dissolved 1.98 g of 3-(2,6-dichlorophenyl)-4-hydroxy-1,2,5-thiadiazole, and 0.8 g of bis(trichloromethyl) carbonate. Thereto, 0.7 g of pyridine was added. The mixture was stirred at room temperature for 12 hours. Thereto, 1.51 g of N-(2-cyanoethyl)-N-methylamine was added. The mixture was stirred at room temperature for 12 hours. The reaction mixture was poured into water, and was extracted with dichloromethane. The dichloromethane layer was washed with dilute hydrochloric acid, 10% sodium hydrogencarbonate, and water successively, dried over anhydrous magnesium sulfate, and concentrated. The concentrate was purified by silica gel column chromatography to obtain 2.8 g of N-(2-cyanoethyl)-N-methyl [3-(2,6-dichlorophenyl)-1,2,5-thiadiazo1-4-yl] carbamate.

후처리

  1. stirringThe mixture was stirred at room temperature for 12 hours
  2. extractionwas extracted with dichloromethane
  3. washThe dichloromethane layer was washed with dilute hydrochloric acid, 10% sodium hydrogencarbonate, and water successively
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe concentrate was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-d2c2e94960ec4b22add88e8173067367
출처 데이터셋
uspto-grants-1999_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05948916

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