N-Methylbenzeneethanamine → HCID 23287661, compound

HRID 367175Notes

Reaction equation

HRID 367175 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][NH:20][CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CC(C)=O.CN(C=O)C>[CH3:19][N:20]([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)[CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

7

Reactant 4

HCID 11503N-MethylbenzeneethanamineHCID 15666Ammonium thiocyanateHCID 24386Thionyl ChlorideHCID 762582-Chloronicotinic acid

Product 1

HCID 23287661HCID 23287661, compoundYield 56.5%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 6228DimethylformamideSolvent

Procedure

The reaction procedure of Example 57 was followed except that 1.792 g (11.37 mmol) of 2-chloronicotinic acid, 15 ml of thionyl chloride, two droplets of DMF, 909 mg of ammonium thiocyanate, 15 ml of acetone, 1.61 g of N-methylphenethylamine and 10 ml of acetone were used. The product was then recrystallized from ethanol to obtain 1.91 g of 2-(N-methyl-N-phenethylamino)-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-a3c2394850bd49f2a85c8550b5b7efa9
Source dataset
uspto-grants-2000_10
Patent number
US06133258

Reaction notes

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