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

HRID 617446Notes

Reaction equation

HRID 617446 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-d2c2e94960ec4b22add88e8173067367
Source dataset
uspto-grants-1999_09
Patent number
US05948916

Reaction notes

Loading…