Ammonium thiocyanate → HCID 23287721, compound

HRID 367182Notes

Reaction equation

HRID 367182 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+].[CH3:19][O:20][C:21]1[CH:22]=[C:23]([CH:27]=[CH:28][CH:29]=1)[NH:24][CH2:25][CH3:26]>CC(C)=O.CN(C=O)C>[CH3:19][O:20][C:21]1[CH:22]=[C:23]([N:24]([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)[CH2:25][CH3:26])[CH:27]=[CH:28][CH:29]=1

Participants

7

Reactant 4

HCID 15666Ammonium thiocyanateHCID 24386Thionyl ChlorideHCID 762582-Chloronicotinic acidHCID 586008N-Ethyl-3-methoxyaniline

Product 1

HCID 23287721HCID 23287721, compoundYield 82.6%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 6228DimethylformamideSolvent

Procedure

The reaction procedure of Example 85 was followed except that 1.891 g (12 mmol) of 2-chloronicotinic acid, 15 ml of thionyl chloride, two droplets of DMF, 960 mg of ammonium thiocyanate, 15 ml of acetone, 1.815 g of 3-methoxy-N-ethylaniline and 10 ml of acetone were used. The resulting crude product was then recrystallized from ethanol to obtain 3.107 g of 2-[N-(3-methoxyphenyl)-N-ethylamino]-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-d7ea1b3548a14f49a874aae067248ac6
Source dataset
uspto-grants-2000_10
Patent number
US06133258

Reaction notes

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