Sodium thiocyanate → 1-(2-Chloro-6-methyl-pyridine-4-carbonyl)-3-(3-methoxy-5-trifluoromethyl-phenyl)-thiourea

HRID 2092217Notes

Reaction equation

HRID 2092217 reaction equation
[S-:1][C:2]#[N:3].[Na+].[Cl:5][C:6]1[CH:11]=[C:10]([C:12](Cl)=[O:13])[CH:9]=[C:8]([CH3:15])[N:7]=1.[CH3:16][O:17][C:18]1[CH:19]=[C:20]([NH2:28])[CH:21]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:23]=1>CC(C)=O.C(Cl)Cl>[Cl:5][C:6]1[CH:11]=[C:10]([C:12]([NH:3][C:2]([NH:28][C:20]2[CH:21]=[C:22]([C:24]([F:26])([F:27])[F:25])[CH:23]=[C:18]([O:17][CH3:16])[CH:19]=2)=[S:1])=[O:13])[CH:9]=[C:8]([CH3:15])[N:7]=1

Participants

6

Reactant 3

HCID 516871Sodium thiocyanateHCID 6056715-(Trifluoromethyl)-m-anisidineHCID 27821302-Chloro-6-methylpyridine-4-carbonyl chloride

Product 1

HCID 594558931-(2-Chloro-6-methyl-pyridine-4-carbonyl)-3-(3-methoxy-5-trifluoromethyl-phenyl)-thiourea

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6344DichloromethaneSolvent

Procedure

Sodium thiocyanate (6.998 g, 0.08632 mol) was added to a solution of 2-chloro-6-methyl-4-pyridinecarbonyl chloride (14.912 g, 0.078472 mol) in acetone (2 l). The resulting mixture was stirred for 1 hour at room temperature (formation of a brown precipitate). Subsequently, 3-methoxy-5-trifluoromethyl benzenamine (15 g, 0.078472 mol) was added dropwise and the reaction mixture was stirred for 2 hours at room temperature (brown precipitate). The mixture was dissolved in CH2Cl2 (1.5 l) and was then washed with 2×250 ml water and brine. The separated organic layer was evaporated and the residue was triturated overnight with DIPE/heptane. The product was filtered off and dried in vacuo. Yield: 21.32 g of intermediate D5 (67%).

Workup

  1. stirringthe reaction mixture was stirred for 2 hours at room temperature (brown precipitate)
  2. washwas then washed with 2×250 ml water and brine
  3. customThe separated organic layer was evaporated
  4. customthe residue was triturated overnight with DIPE/heptane
  5. filtrationThe product was filtered off
  6. customdried in vacuo

Sources & evidence

ORD record
ord-cd8c0f8663934ebb92f5094475ebbe60
Source dataset
uspto-grants-2013_05
Patent number
US08440701B2

Reaction notes

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