Isophthalonitrile → HCID 21935065, compound

HRID 612402Notes

Reaction equation

HRID 612402 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([C:9]#[N:10])[CH:4]=1)#[N:2].C[O-].[Na+].[Cl-:14].[NH4+:15]>CO>[ClH:14].[C:1]([C:3]1[CH:4]=[C:5]([CH:6]=[CH:7][CH:8]=1)[C:9]([NH2:15])=[NH:10])#[N:2]

Participants

5

Reactant 3

HCID 12276IsophthalonitrileHCID 25517Ammonium ChlorideHCID 10942334Sodium Methoxide

Product 1

HCID 21935065HCID 21935065, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In analogy to Example 1 b), from 1,3-dicyanobenzene and sodium methylate in methanol followed by ammonium chloride there is obtained 3-cyano-benzamidine hydrochloride and therefrom with diethyl (2-methoxy-phenoxy)malonate there is obtained rac.-3-[5-(2-methoxy-phenoxy)-4,6-dioxo-1,4,5,6-tetrahydro-pyrimidin-2-yl]-benzonitrile as a white product. From this compound with PCl5 and POCl3 there is obtained 3-[4,6-dichloro-5-(2-methoxy-phenoxy)-pyrimidin-2-yl]-benzonitrile with a melting point of 155-156° from EtOAc. Reaction with 4-tert.-butylbenzenesulphonamide K yields 4-tert.-butyl-N-[6-chloro-2-(3-cyanophenyl)-5-(2-methoxyphenoxy)-pyrimidin-4-yl]-benzenesulphonamide.

Sources & evidence

ORD record
ord-6c8be395b5c246ec8c94aa77a9e03e57
Source dataset
uspto-grants-1999_12
Patent number
US06004965

Reaction notes

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