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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 728644Generated: October 30, 2026

Hydrochloric Acid → (+/-)-cis-4-[[2-Amino-6-chloro-5-[(4-chlorophenyl)azo]-4-pyrimidinyl]amino]-2-cyclopentene-1-methanol

https://huagongshe.com/reaction/728644

Reaction equation

Participants

RoleNameHCIDCharge
ReactantHydrochloric AcidHCID 313—
Reactant4-ChloroanilineHCID 7812—
Reactant(+)-cis-4-[(2-Amino-4-chloro-6-pyrimidinyl)amino]-2-cyclopentene-1-methanolHCID 11746763—
ReactantSodium Acetate TrihydrateHCID 23665404—
ReactantSodium NitriteHCID 23668193—
SolventAcetic AcidHCID 176—
SolventWaterHCID 962—
ProductBenzenediazonium, 4-chloro-, chlorideHCID 11819533—
Product(+/-)-cis-4-[[2-Amino-6-chloro-5-[(4-chlorophenyl)azo]-4-pyrimidinyl]amino]-2-cyclopentene-1-methanolHCID 145030706,623.7%

Reaction Steps

(±)-cis-4-[(2-Amino-4-chloro-6-pyrimidinyl)amino]-2-cyclopentene-1-methanol from Example 1 (11.58 g, 48 1 mmol) and sodium acetate trihydrate (97 g) were dissolved in glacial acetic acid (225 mL) and water (225 mL). A cold solution (0.5° C.) of 4-chlorobenzenediazonium chloride was prepared from 4-chloroaniline (6.74 g, 52.8 mol), concentrated hydrochloric acid (14.7 mL) water (52 mL), and sodium nitrite (4.01 g, 58.2 mmol in 47 mL of water). Tbis cold solution was added dropwise over 5 minutes to the first solution. The resulting yellow precipitate was filtered after 18 hours, washed with water, and extracted with ethanol to give title compound as dark yellow powder (12.56 g, 69%), m.p. 218-220° C. dec.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS05049671
Source datasetuspto-grants-1991_09
ORD IDord-70ef8fafeb2944e78c8d4762db3ce540
Source noteuspto-grants-1991_09