Pyridine → HCID 178522642, compound

HRID 703766Notes

Reaction equation

HRID 703766 reaction equation
[NH2:1][C:2]1[S:3][C:4]([SH:7])=[N:5][N:6]=1.N1C=CC=CC=1.[C:14](Cl)(=[O:22])[O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CC(N(C)C)=O>[SH:7][C:4]1[S:3][C:2]([NH:1][C:14]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:22])=[N:6][N:5]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 15891Phenyl chloroformateHCID 178509208HCID 178509208, compound

Product 1

HCID 178522642HCID 178522642, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
0 °C

Procedure

61 g of 2-amino-5-mercapto-1,3,4-thiadiazole were dissolved in 230 ml of dimethylacetamide, and 40.8 ml of pyridine were added thereto. The resulting solution was cooled to a temperature not higher than 0° C., and 79 g of phenyl chlorocarbonate were added dropwise thereto. After completion of the dropwise addition, the solution was stirred for 1.5 hours at a temperature not higher than 0° C., and the reaction mixture was then poured into 1 liter of ice-water. Precipitated crystals were collected by filtration and recrystallized from acetonitrile to obtain the desired product.

Workup

  1. additionAfter completion of the dropwise addition
  2. customPrecipitated crystals
  3. filtrationwere collected by filtration
  4. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-16f9bd63bbe24003b2800fd052fb92ae
Source dataset
uspto-grants-1991_01
Patent number
US04985348

Reaction notes

Loading…