2-Chloro-6-methylpyridine-4-carbonyl chloride → 1-(2-Chloro-6-methyl-pyridine-4-carbonyl)-3-(3-fluoro-5-methoxy-phenyl)thiourea

HRID 2092224Notes

Reaction equation

HRID 2092224 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8](Cl)=[O:9])[CH:5]=[C:4]([CH3:11])[N:3]=1.[N-:12]=[C:13]=[S:14].[NH4+].[F:16][C:17]1[CH:18]=[C:19]([NH2:25])[CH:20]=[C:21]([O:23][CH3:24])[CH:22]=1>CC(C)=O>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([NH:12][C:13]([NH:25][C:19]2[CH:20]=[C:21]([O:23][CH3:24])[CH:22]=[C:17]([F:16])[CH:18]=2)=[S:14])=[O:9])[CH:5]=[C:4]([CH3:11])[N:3]=1

Participants

5

Reactant 3

HCID 27821302-Chloro-6-methylpyridine-4-carbonyl chlorideHCID 404278903-Fluoro-5-methoxyanilineHCID 178514171HCID 178514171, compound

Product 1

HCID 594558951-(2-Chloro-6-methyl-pyridine-4-carbonyl)-3-(3-fluoro-5-methoxy-phenyl)thiourea

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

2-Chloro-6-methyl-4-pyridinecarbonyl chloride (44.087 g, 0.232 mol) in acetone (1 l) was treated with ammonium isothiocyanate (21.192 g, 0.278 mol) and the mixture was stirred for 1 hour at room temperature. Subsequently, a solution of 3-fluoro-5-methoxybenzenamine (36.02 g, 0.255 mol) in acetone (200 ml) was added dropwise and the reaction mixture was stirred for 4 hours at room temperature. The solvent was evaporated in vacuo and the residue was dissolved in CH2Cl2 (1 l). This organic solution was washed (H2O), dried (MgSO4), filtered and the solvent was evaporated in vacuo to yield a brown solid. The brown solid was triturated in acetonitrile (0.8 l), stirred overnight and the solid was filtered off and dried (vacuum oven, 4 hours at 65° C.). Yield: 59.69 g of intermediate D13 (73%).

Workup

  1. stirringthe reaction mixture was stirred for 4 hours at room temperature
  2. customThe solvent was evaporated in vacuo
  3. dissolutionthe residue was dissolved in CH2Cl2 (1 l)
  4. washThis organic solution was washed (H2O)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent was evaporated in vacuo
  8. customto yield a brown solid
  9. customThe brown solid was triturated in acetonitrile (0.8 l)
  10. stirringstirred overnight
  11. filtrationthe solid was filtered off
  12. customdried (vacuum oven, 4 hours at 65° C.)

Sources & evidence

ORD record
ord-c5486371947940ef86f860c85eecbd7a
Source dataset
uspto-grants-2013_05
Patent number
US08440701B2

Reaction notes

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