Phosphorus pentachloride → 2-Ethoxyimino-2-(5-amino-1,2,4-thiadiazol-3-yl)acetyl chloride hydrochloride

HRID 1247919Notes

Reaction equation

P(Cl)(Cl)(Cl)(Cl)[Cl:2].[CH2:7]([O:9][N:10]=[C:11]([C:15]1[N:19]=[C:18]([NH2:20])[S:17][N:16]=1)[C:12](O)=[O:13])[CH3:8]>C(Cl)Cl>[ClH:2].[CH2:7]([O:9][N:10]=[C:11]([C:15]1[N:19]=[C:18]([NH2:20])[S:17][N:16]=1)[C:12]([Cl:2])=[O:13])[CH3:8]

Participants

Conditions

Temperature: -20 °C

Procedure

To a solution of phosphorus pentachloride (54.6 g) in methylene chloride (500 ml) was added 2-ethoxyimino-2-(5-amino-1,2,4-thiadiazol-3-yl)-acetic acid (syn isomer) (54.0 g) under stirring and cooling at -20° C. The mixture was stirred for 30 minutes at -15° to -12° C. and for 2 hours at -5° C. To the mixture containing precipitates of an object compound was added diisopropyl ether (500 ml) at -5° C. and the mixture was stirred for 30 minutes at -5° to 10° C. The resulting precipitates were collected by filtration, washed with diisopropyl ether and dried to give 2-ethoxyimino-2-(5-amino-1,2,4-thiadiazol-3-yl)acetyl chloride hydrochloride (syn isomer) (60.17 g), mp. 125° to 127° C. (dec.).

Workup

stirringThe mixture was stirred for 30 minutes at -15° to -12° C. and for 2 hours at -5° C
additionTo the mixture containing
customprecipitates of an object compound
additionwas added diisopropyl ether (500 ml) at -5° C.
stirringthe mixture was stirred for 30 minutes at -5° to 10° C
customThe resulting precipitates
filtrationwere collected by filtration
washwashed with diisopropyl ether
customdried

Sources & evidence

ORD record: ord-a60d222d80fe4e3490d723d8730a3689
Source dataset: uspto-grants-1985_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04521413

Reaction notes

Loading…