Ammonium thiocyanate → HCID 9840343, compound

HRID 367171Notes

Reaction equation

HRID 367171 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]2[O:28][CH2:29][O:30][C:24]=2[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]2[O:28][CH2:29][O:30][C:24]=2[CH:23]=1)[CH3:20]

Participants

7

Reactant 4

HCID 15666Ammonium thiocyanateHCID 24386Thionyl ChlorideHCID 762582-Chloronicotinic acidHCID 1183651,3-Benzodioxol-5-amine, N-ethyl-

Product 1

HCID 9840343HCID 9840343, compoundYield 57.9%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 6228DimethylformamideSolvent

Procedure

The reaction procedure of Example 57 was followed except that 1.585 mg (10.08 mmol) of 2-chloronicotinic acid, 15 ml of thionyl chloride, two droplets of DMF, 844 mg of ammonium thiocyanate, 15 ml of acetone, 1.83 g of N-ethyl-3,4-methylenedioxyaniline and 10 ml of acetone were used. The resulting crude product was then recrystallized from a mixture of ethanol and ether to obtain 1.91 g of 2-[N-ethyl-N-(3,4-methylenedioxyphenyl)amino]-4H-pyrido[3,2-e]-1,3-thiazin-4-one.

Workup

  1. customThe reaction procedure of Example 57
  2. customThe resulting crude product was then recrystallized from a mixture of ethanol and ether

Sources & evidence

ORD record
ord-78a26fd0f7d149cab5d15f33fd34a96d
Source dataset
uspto-grants-2000_10
Patent number
US06133258

Reaction notes

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