Ammonium thiocyanate → HCID 23287588, compound

HRID 367202Notes

Reaction equation

HRID 367202 reaction equation
Cl[C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[S-:11][C:12]#[N:13].[NH4+].[OH:15][CH:16]1[CH2:21][CH2:20][CH2:19][NH:18][CH2:17]1>S(Cl)(Cl)=O>[OH:15][CH:16]1[CH2:21][CH2:20][CH2:19][N:18]([C:12]2[S:11][C:2]3[N:10]=[CH:9][CH:8]=[CH:7][C:3]=3[C:4](=[O:6])[N:13]=2)[CH2:17]1

Participants

5

Reactant 3

HCID 15666Ammonium thiocyanateHCID 232933-HydroxypiperidineHCID 762582-Chloronicotinic acid

Product 1

HCID 23287588HCID 23287588, compoundYield 17.1%

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

The reaction procedure of Example 106 was followed except that 1.0 g of 2-chloronicotinic acid, 10 ml of thionyl chloride, 531 mg of ammonium thiocyanate and 642 mg of 3-hydroxypiperidine were used. The product was subjected to separation through silica gel column chromatography (eluant: 50:1:0.1 mixture of chloroform, methanol and aqueous ammonia), and then recrystallized from a mixture of isopropyl ether and isopropanol to obtain 285 mg of 2-(3-hydroxypiperidino)-4H-pyrido[3,2-e]-1,3-thiazin-4-one.

Workup

  1. customThe reaction procedure of Example 106
  2. customThe product was subjected to separation through silica gel column chromatography (eluant: 50:1:0.1 mixture of chloroform, methanol and aqueous ammonia)
  3. customrecrystallized from a mixture of isopropyl ether and isopropanol

Sources & evidence

ORD record
ord-b82f871db2b749f6b41bda2ced6796a1
Source dataset
uspto-grants-2000_10
Patent number
US06133258

Reaction notes

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