Ethyl Acetate → HCID 14477681, compound

HRID 653848Notes

Reaction equation

HRID 653848 reaction equation
[C:1]([NH:20][C:21]1[S:25][N:24]=[C:23](/[C:26](=[N:32]/[OH:33])/[C:27]([O:29][CH2:30][CH3:31])=[O:28])[N:22]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:41][F:42].C(OCC)(=O)C>CS(C)=O>[C:1]([NH:20][C:21]1[S:25][N:24]=[C:23](/[C:26](=[N:32]/[O:33][CH2:41][F:42])/[C:27]([O:29][CH2:30][CH3:31])=[O:28])[N:22]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 61108BromofluoromethaneHCID 136421289HCID 136421289, compound

Product 1

HCID 14477681HCID 14477681, compoundYield 90.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Ethyl 2-(5-tritylamino-1,2,4-thiadiazol-3-yl)-(Z)-2-hydroxyiminoacetate (60.4 g) was dissolved in dimethyl sulfoxide (210 ml). Potassium carbonate (96.48 g) was added under ice cooling, followed by stirring for 10 minutes. Bromofluoromethane (19 g) was added further, followed by stirring at room temperature for 3 hours. The reaction mixture was added with ethyl acetate (1 l) and washed with water and then with saturated saline. Anhydrous magnesium sulfate was added to the thus-washed reaction mixture to dry the same. The solvent was distilled off, and ethanol (120 ml) was added to the residue. Deposited crystals were collected by filtration and then washed with ethanol to obtain the target product (58.2 g). Infrared spectrum (cm- 1, Nujol) 1735, 1530.

Workup

  1. stirringby stirring at room temperature for 3 hours
  2. washwashed with water
  3. additionAnhydrous magnesium sulfate was added to the thus-washed reaction mixture
  4. customto dry the same
  5. distillationThe solvent was distilled off
  6. additionethanol (120 ml) was added to the residue
  7. filtrationDeposited crystals were collected by filtration
  8. washwashed with ethanol

Sources & evidence

ORD record
ord-369f5a6007044c1792f6e87b1d01ad6d
Source dataset
uspto-grants-1992_07
Patent number
US05128465

Reaction notes

Loading…