Ammonium thiocyanate → HCID 23287664, compound

HRID 367177Notes

Reaction equation

HRID 367177 reaction equation
Cl[C:2]1[N:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.S(Cl)(Cl)=O.[S-:16][C:17]#[N:18].[NH4+].[CH3:20][NH:21][C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=1>CC(C)=O.CN(C=O)C>[Cl:28][C:25]1[CH:26]=[CH:27][C:22]([N:21]([C:17]2[S:16][C:2]3[N:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:3]=3[C:4](=[O:6])[N:18]=2)[CH3:20])=[CH:23][CH:24]=1

Participants

7

Reactant 4

HCID 15666Ammonium thiocyanateHCID 24386Thionyl ChlorideHCID 702724-Chloro-N-methylbenzenamineHCID 1217242-Chloro-6-methylnicotinic acid

Product 1

HCID 23287664HCID 23287664, compoundYield 39.2%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 6228DimethylformamideSolvent

Procedure

The reaction procedure of Example 57 was followed except that 2.175 g (12.68 mmol) of 2-chloro-6-methylnicotinic acid, 15 ml of thionyl chloride, two droplets of DMF, 1.01 g of ammonium thiocyanate, 15 ml of acetone, 1.81 g of N-methyl-4-chloroaniline and 10 ml of acetone were used. The resulting crude product was then recrystallized from ethanol to obtain 1.58 g of 2-[N-(4-chlorophenyl)-N-methylamino)-7-methyl-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 ethanol

Sources & evidence

ORD record
ord-db396253b43b4945b8536457ec6538b6
Source dataset
uspto-grants-2000_10
Patent number
US06133258

Reaction notes

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