Ammonium thiocyanate → 1-(2-Chloro-6-methyl-pyridine-4-carbonyl)-3-(3,4-difluoro-phenyl)-thiourea

HRID 2092214Notes

Reaction equation

HRID 2092214 reaction equation
[NH4+].[N:2]#[C:3][S-:4].[Cl:5][C:6]1[CH:11]=[C:10]([C:12](Cl)=[O:13])[CH:9]=[C:8]([CH3:15])[N:7]=1.[F:16][C:17]1[CH:18]=[C:19]([NH2:24])[CH:20]=[CH:21][C:22]=1[F:23]>CC(C)=O>[Cl:5][C:6]1[CH:11]=[C:10]([C:12]([NH:2][C:3]([NH:24][C:19]2[CH:20]=[CH:21][C:22]([F:23])=[C:17]([F:16])[CH:18]=2)=[S:4])=[O:13])[CH:9]=[C:8]([CH3:15])[N:7]=1

Participants

5

Reactant 3

HCID 15666Ammonium thiocyanateHCID 774693,4-DifluoroanilineHCID 27821302-Chloro-6-methylpyridine-4-carbonyl chloride

Product 1

HCID 594558971-(2-Chloro-6-methyl-pyridine-4-carbonyl)-3-(3,4-difluoro-phenyl)-thiourea

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Thiocyanic acid ammonium salt (10.6 g) was added to a mixture of 2-chloro-6-methyl-4-pyridinecarbonyl chloride (22.04 g; 116 mmol) and acetone (400 ml). The reaction mixture was stirred for 30 minutes and then 3,4-difluorobenzenamine (14.98 g; 116 mmol) was added slowly via an additional funnel. The resulting solution was stirred for 2 hours, quenched by water (100 ml) and then extracted by CH2Cl2 (3×100 ml). The combined organic phase was dried over MgSO4, filtered and the solvent was evaporated in vacuo. Yield: 38.1 g of intermediate D1.

Workup

  1. stirringThe resulting solution was stirred for 2 hours
  2. customquenched by water (100 ml)
  3. extractionextracted by CH2Cl2 (3×100 ml)
  4. dry with materialThe combined organic phase was dried over MgSO4
  5. filtrationfiltered
  6. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-588229d49bc44791b8b62b06c65ab7c6
Source dataset
uspto-grants-2013_05
Patent number
US08440701B2

Reaction notes

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