Ammonium thiocyanate → HCID 23287666, compound

HRID 367183Notes

Reaction equation

HRID 367183 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]([CH:28]([CH3:30])[CH3:29])=[CH:24][CH:23]=1)[CH3:20]>CC(C)=O.CN(C=O)C>[CH2:19]([N:21]([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:22]1[CH:27]=[CH:26][C:25]([CH:28]([CH3:29])[CH3:30])=[CH:24][CH:23]=1)[CH3:20]

Participants

7

Reactant 4

HCID 15666Ammonium thiocyanateHCID 24386Thionyl ChlorideHCID 762582-Chloronicotinic acidHCID 23287593N-Ethyl-4-(propan-2-yl)aniline

Product 1

HCID 23287666HCID 23287666, compoundYield 68.9%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 6228DimethylformamideSolvent

Procedure

The reaction procedure of Example 85 was followed except that 2.347 g (15.1 mmol) of 2-chloronicotinic acid, 30 ml of thionyl chloride, three droplets of DMF, 1.262 g of ammonium thiocyanate, 15 ml of acetone, 2.583 g of N-ethyl-4-isopropylaniline and 10 ml of acetone were used. The resulting crude product was then recrystallized from a mixture of ethanol, ether and hexane to obtain 3.388 g of 2-[N-ethyl-N-(4-isopropylphenyl)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 a mixture of ethanol, ether and hexane

Sources & evidence

ORD record
ord-8f60c2da84a04cf3a94be71365810dd1
Source dataset
uspto-grants-2000_10
Patent number
US06133258

Reaction notes

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