Sodium Hydroxide → HCID 14620461, compound

HRID 653852Notes

Reaction equation

HRID 653852 reaction equation
[C:1]([NH:20][C:21]1[S:25][N:24]=[C:23]([C:26](=O)[C:27]([OH:29])=[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.[F:31][CH2:32][O:33][NH2:34].[OH-].[Na+]>C(O)C.O>[C:1]([NH:20][C:21]1[S:25][N:24]=[C:23](/[C:26](=[N:34]/[O:33][CH2:32][F:31])/[C:27]([OH:29])=[O:28])[N:22]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 11412339HCID 11412339, compoundHCID 13713208HCID 13713208, compound

Product 1

HCID 14620461HCID 14620461, compoundYield 49.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

2-(5-Tritylamino-1,2,4-thiadiazol-3-yl)-2-oxoacetic acid (1 g) was added to a mixture of a solution of fluoromethoxyamine (0.58 g) in ethanol (25 ml) and water (0.45 ml). After adjusting the pH of the resulting mixture to 4-5 with a 10% aqueous solution of sodium hydroxide, the mixture was stirred overnight at room temperature. The solvent was distilled off under reduced pressure, followed by addition of water (20 ml) and sodium chloride (10 g) to the residue. The pH of the resulting solution was adjusted to 1 with concentrated hydrochloric acid. The solution was extracted four times with ethyl acetate (30 ml). After washing the extract with saturated saline, anhydrous magnesium sulfate was added to the extract to dry the same. The dry was distilled off and the residue was crystallized from a 1:10 mixture of acetone and isopropyl ether, thereby obtaining the target product (0.55 g).

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. additionfollowed by addition of water (20 ml) and sodium chloride (10 g) to the residue
  3. extractionThe solution was extracted four times with ethyl acetate (30 ml)
  4. washAfter washing the
  5. extractionextract with saturated saline, anhydrous magnesium sulfate
  6. additionwas added to the
  7. extractionextract
  8. customto dry the same
  9. distillationThe dry was distilled off
  10. customthe residue was crystallized from a 1:10 mixture of acetone and isopropyl ether

Sources & evidence

ORD record
ord-1cda0fc0a362431390c4a3eee9c3b010
Source dataset
uspto-grants-1992_07
Patent number
US05128465

Reaction notes

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