4-Aminobenzonitrile → HCID 23287603, compound

HRID 367112Notes

Reaction equation

HRID 367112 reaction equation
Cl[C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[S-:11][C:12]#[N:13].[NH4+].[C:15]([C:17]1[CH:23]=[CH:22][C:20]([NH2:21])=[CH:19][CH:18]=1)#[N:16]>S(Cl)(Cl)=O>[C:15]([C:17]1[CH:23]=[CH:22][C:20]([NH:21][C:12]2[S:11][C:2]3[N:10]=[CH:9][CH:8]=[CH:7][C:3]=3[C:4](=[O:6])[N:13]=2)=[CH:19][CH:18]=1)#[N:16]

Participants

5

Reactant 3

HCID 133964-AminobenzonitrileHCID 15666Ammonium thiocyanateHCID 762582-Chloronicotinic acid

Product 1

HCID 23287603HCID 23287603, compoundYield 81.3%

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

The reaction procedure of Example 6 was followed except that 3.60 g (30.64 mmol) of 2-chloronicotinic acid, 20 ml of thionyl chloride, 2.33 g of ammonium thiocyanate and 3.55 g of 4-cyanoaniline were used. As a result, 6.85 g of 2-(4-cyanoanilino)-4H-pyrido[3,2-e]-1,3-thiazin-4-one was obtained.

Workup

  1. customThe reaction procedure of Example 6

Sources & evidence

ORD record
ord-c54df5d5d9144a46a152607188a717d2
Source dataset
uspto-grants-2000_10
Patent number
US06133258

Reaction notes

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