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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 9104Generated: October 25, 2026

Formaldehyde → N-(6-Cyano-1,3-benzothiazol-2-yl)-N'-(3-pyridylmethyl)urea

https://huagongshe.com/reaction/9104

Reaction equation

Participants

RoleNameHCIDCharge
ReactantFormaldehydeHCID 712—
ReactantMethylamineHCID 6329—
Reactant4-MethylmorpholineHCID 7972—
ReactantN-Ethyl-N'-(6-nitro-1,3-benzothiazol-2-yl)ureaHCID 9813955—
Reactant1-Ethyl-5-methyl-3-(6-nitro-1,3-benzothiazol-2-yl)-1,3,5-triazinan-2-oneHCID 21985532—
SolventMethanolHCID 887—
SolventWater ethanolHCID 19096565—
ProductN-(6-Cyano-1,3-benzothiazol-2-yl)-N'-(3-pyridylmethyl)ureaHCID 21985518—

Reaction Conditions

Temperature80 °C

Reaction Steps

General procedure for synthesizing 1-ethyl-5-methyl-3-(6-nitro-1,3-benzothiazol-2-yl)-1,3,5-triazinan-2-one: N-Ethyl-N′-(6-nitro-1,3-benzothiazol-2-yl)urea is suspended in an alkanol/water mixture, preferably 1:1 EtOH/H2O at room temperature. A 37% aqueous solution of formaldehyde is added followed by addition of a 2M solution of MeNH2 in MeOH, then about 2 mole equivalents of N-methylmorpholine. The solution is warmed to about 70–85° C., preferably 80° C., then allowed to stir for about 4–24 hours, preferably 4 hours. The slurry is then cooled to room temperature, filtered and washed well with water, dried and the title product is isolated. General Procedure for Grignard Addition:

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07091227B2
Source datasetuspto-grants-2006_08
ORD IDord-e8b7ee04ec75448d86e69b5a0568d5fc
Source noteuspto-grants-2006_08