Ethyl Acetate → HCID 14477681, compound

HRID 1651755Notes

Reaction equation

HRID 1651755 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 dimethylsulfoxide (210 ml), followed by an addition of potassium carbonate (96.48 g) under ice-cooling. The resulting mixture was stirred for 10 minutes. Bromofluoromethane (19 g) was thereafter added, followed by stirring at room temperature for 3 hours. Ethyl acetate (1 l) was added to the reaction mixture. The resulting mixture was washed with water and then with saturated saline, and was added with anhydrous magnesium sulfate to dry the mixture. The solvent was distilled out and ethanol (120 ml) was added to the residue. Crystals thus precipitated were collected by filtration and then washed to obtain 58.2 g of the title compound.

Workup

  1. temperaturecooling
  2. stirringby stirring at room temperature for 3 hours
  3. washThe resulting mixture was washed with water
  4. additionwith saturated saline, and was added with anhydrous magnesium sulfate
  5. customto dry the mixture
  6. distillationThe solvent was distilled out and ethanol (120 ml)
  7. additionwas added to the residue
  8. customCrystals thus precipitated
  9. filtrationwere collected by filtration
  10. washwashed

Sources & evidence

ORD record
ord-74331adfcaaa4064a2c568094f0b5647
Source dataset
uspto-grants-1990_05
Patent number
US04929612

Reaction notes

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