Ammonium thiocyanate → 2-[N-(4-bromophenyl)-N-ethylamino)-4H-pyrido[3,2-e]-1,3-thiazin-4-one

HRID 367160

Reaction equation

HRID 367160 reaction equation
Cl[C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.S(Cl)(Cl)=O.[S-:15][C:16]#[N:17].[NH4+].[CH2:19]([NH:21][C:22]1[CH:27]=[CH:26][C:25]([Br:28])=[CH:24][CH:23]=1)[CH3:20]>CC(C)=O.CN(C=O)C>[Br:28][C:25]1[CH:26]=[CH:27][C:22]([N:21]([C:16]2[S:15][C:2]3[N:10]=[CH:9][CH:8]=[CH:7][C:3]=3[C:4](=[O:6])[N:17]=2)[CH2:19][CH3:20])=[CH:23][CH:24]=1

Participants

7

Reactant 4

HCID 15666Ammonium thiocyanateHCID 24386Thionyl ChlorideHCID 762582-Chloronicotinic acidHCID 117456564-bromo-N-ethylaniline

Product 1

HCID 232875742-[N-(4-bromophenyl)-N-ethylamino)-4H-pyrido[3,2-e]-1,3-thiazin-4-oneYield 75.3%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 6228DimethylformamideSolvent

Procedure

The reaction procedure of Example 57 was followed except that 1.203 g (7.63 mmol) of 2-chloronicotinic acid, 15 ml of thionyl chloride, two droplets of DMF, 639 mg of ammonium thiocyanate, 15 ml of acetone, 1.53 g of N-ethyl-4-bromoaniline and 10 ml of acetone were used. The product was then recrystallized from ethanol to obtain 2.08 g of 2-[N-(4-bromophenyl)-N-ethylamino)-4H-pyrido[3,2-e]-1,3-thiazin-4-one.

Workup

  1. customThe reaction procedure of Example 57
  2. customThe product was then recrystallized from ethanol

Sources & evidence

ORD record
ord-fa28f574ce1144d4a70656d542ed6a6a
Source dataset
uspto-grants-2000_10
Patent number
US06133258

Linked notes

Loading…