Diisopropyl Ether → 2-(5-Amino-1,2,4-thiadiazol-3-yl)-2-fluoromethoxyiminoacetyl chloride . hydrochloride

HRID 22479Notes

Reaction equation

HRID 22479 reaction equation
O.[NH2:2][C:3]1[S:7][N:6]=[C:5]([C:8](=[N:12][O:13][CH2:14][F:15])[C:9](O)=[O:10])[N:4]=1.P(Cl)(Cl)(Cl)(Cl)[Cl:17].C(OC(C)C)(C)C>C(Cl)Cl>[ClH:17].[NH2:2][C:3]1[S:7][N:6]=[C:5]([C:8](=[N:12][O:13][CH2:14][F:15])[C:9]([Cl:17])=[O:10])[N:4]=1

Participants

5

Reactant 3

HCID 7914Diisopropyl EtherHCID 24819Phosphorus pentachlorideHCID 1317190322-(5-Amino-1,2,4-thiadiazol-3-yl)-2-fluoromethoxyiminoacetic acid hydrate

Product 1

HCID 727321862-(5-Amino-1,2,4-thiadiazol-3-yl)-2-fluoromethoxyiminoacetyl chloride . hydrochlorideYield 106%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 50 ml of methylene chloride, 10.0 g (0.044 mol) of 2-(5-amino-1,2,4-thiadiazol-3-yl)-2-fluoromethoxyiminoacetic acid hydrate were suspended, followed by the addition of 13.3 g (0.064 mol) of phosphorus pentachloride at -20° C. After stirring for 30 minutes, 100 ml of isopropyl ether were added dropwise to the reaction mixture to precipitate crystals. The resulting crystals were collected by filtration, washed with 20 ml of isopropyl ether and then dried, whereby 9.33 g of a title compound were obtained (yield: 77%, purity: 89.7%).

Workup

  1. customto precipitate crystals
  2. filtrationThe resulting crystals were collected by filtration
  3. washwashed with 20 ml of isopropyl ether
  4. customdried

Sources & evidence

ORD record
ord-18bf9a7224234c39aa73ac684dbac015
Source dataset
uspto-grants-1995_06
Patent number
US05428173

Reaction notes

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