Ammonium thiocyanate → HCID 23287598, compound

HRID 367184Notes

Reaction equation

HRID 367184 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+].[C:19]([C:22]1[CH:30]=[CH:29][C:25]([NH:26][CH2:27][CH3:28])=[CH:24][CH:23]=1)(=[O:21])[CH3:20]>CC(C)=O.CN(C=O)C>[CH2:27]([N:26]([C:16]1[S:15][C:2]2[N:10]=[CH:9][CH:8]=[CH:7][C:3]=2[C:4](=[O:6])[N:17]=1)[C:25]1[CH:29]=[CH:30][C:22]([C:19](=[O:21])[CH3:20])=[CH:23][CH:24]=1)[CH3:28]

Participants

7

Reactant 4

HCID 15666Ammonium thiocyanateHCID 24386Thionyl ChlorideHCID 762582-Chloronicotinic acidHCID 3136934-acetyl-N-ethylaniline

Product 1

HCID 23287598HCID 23287598, compoundYield 83.9%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 6228DimethylformamideSolvent

Procedure

The reaction procedure of Example 85 was followed except that 1.576 g (10 mmol) of 2-chloronicotinic acid, 10 ml of thionyl chloride, two droplets of DMF, 837 mg of ammonium thiocyanate, 10 ml of acetone, 3.986 g of 4-acetyl-N-ethylaniline and 10 ml of acetone were used. The resulting crude product was then recrystallized from ethanol to obtain 2.729 g of 2-[N-ethyl-N-(4-acetylphenyl)amino]-4H-pyrido[3,2-e]-1,3-thiazin-4-one.

Workup

  1. customThe reaction procedure of Example 85
  2. customThe resulting crude product was then recrystallized from ethanol

Sources & evidence

ORD record
ord-4737295f0db04dd9869ae216cba75857
Source dataset
uspto-grants-2000_10
Patent number
US06133258

Reaction notes

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