2,4,6-Trichloroaniline → HCID 70545492, compound

HRID 848702Notes

Reaction equation

HRID 848702 reaction equation
[Cl:1][C:2]1[CH:8]=[C:7]([Cl:9])[CH:6]=[C:5]([Cl:10])[C:3]=1[NH2:4].[C:11]([C:13](=[CH:22]OCC)[C:14]([NH:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[O:15])#[N:12]>C(O)C>[C:11]([C:13](=[CH:22][NH:4][C:3]1[C:2]([Cl:1])=[CH:8][C:7]([Cl:9])=[CH:6][C:5]=1[Cl:10])[C:14]([NH:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[O:15])#[N:12]

Participants

4

Reactant 2

HCID 124712,4,6-TrichloroanilineHCID 230015ethyl N-(2-cyano-3-ethoxyacryloyl)carbamate

Product 1

HCID 70545492HCID 70545492, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2,4,6-Trichloroaniline (0.04 mol) is reacted with α-cyano-β-ethoxy-N-ethoxycarbonylacrylamide (0.04 mol) by heating at reflux in ethanol to yield α-cyano-β-(2,4,6-trichloroanilino)-N-ethoxycarbonylacrylamide, which is cyclized by heating at reflux in 1,2-dichlorobenzene to yield crude product which is chromatographed on silica eluting with chloroform/acetone (3/1) to 5-cyano-1-(2,4,6-trichlorophenyl)uracil, pale yellow crystals, m.p. 245°-247°.

Workup

  1. temperatureby heating

Sources & evidence

ORD record
ord-a9b1121f31b0477cbc3f0780bec371c9
Source dataset
uspto-grants-1981_10
Patent number
US04297297

Reaction notes

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