1,4-Dicyanobenzene → HCID 13980727, compound

HRID 612403Notes

Reaction equation

HRID 612403 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]#[N:10])=[CH:5][CH:4]=1)#[N:2].C[O-].[Na+].[Cl-:14].[NH4+:15]>CO>[ClH:14].[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]([NH2:15])=[NH:10])=[CH:5][CH:4]=1)#[N:2]

Participants

5

Reactant 3

HCID 121721,4-DicyanobenzeneHCID 25517Ammonium ChlorideHCID 10942334Sodium Methoxide

Product 1

HCID 13980727HCID 13980727, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

From 1,4-dicyanobenzene and sodium methylate in methanol followed by ammonium chloride there is obtained 4-cyano-benzamidine hydrochloride, which is used in the next step without further purification, and therefrom with diethyl (2-methoxy-phenoxy)-malonate there is obtained rac.-4-[5-(2-methoxy-phenoxy)-4,6-dioxo-1,4,5,6-tetrahydro-pyrimidin-2-yl]-benzo-nitrile as a yellow product with a melting point >250° C. With PCl5 and POCl3 this compound yields 4-[4,6-dichloro-5-(2-methoxy-phenoxy)-pyrimidin-2-yl]-benzonitrile as a brownish material of melting point 179-180° C. from EtOAc. Reaction with 4-tert.-butyl-benzenesulphonamide K finally yields 4-tert.-butyl-N-[6-chloro-2-(4-cyanophenyl)-5-(2-methoxy-phenoxy)-pyrimidin-4-yl]-benzenesulphonamide.

Sources & evidence

ORD record
ord-3cf2b7e03d9f4eee9b9a7936727bac44
Source dataset
uspto-grants-1999_12
Patent number
US06004965

Reaction notes

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