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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1088754Generated: October 31, 2026

Chloroacetyl chloride → 4-(Chloroacetyl)-7-(4-chlorophenyl)-4.5-dihydro-6-methylpyrazolo[1,5-a]pyrimidine-3-carbonitrile

https://huagongshe.com/reaction/1088754

Reaction equation

Participants

RoleNameHCIDCharge
ReactantChloroacetyl chlorideHCID 6577—
ReactantProton spongeHCID 88675—
Reactant7-(4-Chlorophenyl)-4,5-dihydro-6-methylpyrazolo[1,5-a]pyrimidine-3-carbonitrileHCID 136102889—
SolventTetrahydrofuranHCID 8028—
Product4-(Chloroacetyl)-7-(4-chlorophenyl)-4.5-dihydro-6-methylpyrazolo[1,5-a]pyrimidine-3-carbonitrileHCID 15101089—

Reaction Steps

A 10 g portion of 7-(4-chlorophenyl)-4,5-dihydro-6-methylpyrazolo[1,5-a]pyrimidine-3-carbonitrile and 9 g of [1,8-bis(dimethylamino)naphthalene, N,N,N',N'-tetramethyl-1,8-naphthalenediamine] in 300 ml of dry tetrahydrofuran under nitrogen was mixed and 6 ml of chloroacetyl chloride in 70 ml of dry tetrahydrofuran was added over 15 minutes with stirring. The mixture was stirred at reflux for 5.5 hours, then at room temperature overnight and then filtered. The filtrate was concentrated to an oil. This oil was triturated with ether, the solid collected and dried, giving 10 g of the desired intermediate, mp 138°-140° C.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS04963553
Source datasetuspto-grants-1990_10
ORD IDord-699e96818ed14b6a88ef7e38216c7c1e
Source noteuspto-grants-1990_10