Acetic Acid → 4-Amino-5-fluoro-2-(3-methylpicolinoyl)phenyl thiocyanate

HRID 48975

Reaction equation

HRID 48975 reaction equation
[CH3:1][C:2]1[C:3]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[C:12]([NH2:17])[CH:11]=2)=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1.[S-:18][C:19]#[N:20].[Na+].C(O)(=O)C.BrBr>O>[NH2:17][C:12]1[C:13]([F:16])=[CH:14][C:15]([S:18][C:19]#[N:20])=[C:10]([C:8](=[O:9])[C:3]2[C:2]([CH3:1])=[CH:7][CH:6]=[CH:5][N:4]=2)[CH:11]=1

Participants

6

Reactant 4

HCID 176Acetic Acid2×HCID 24408BromineHCID 516871Sodium thiocyanateHCID 120568333-Amino-4-fluorophenyl 3-methyl-2-pyridyl ketone

Product 1

HCID 111969574-Amino-5-fluoro-2-(3-methylpicolinoyl)phenyl thiocyanateYield 100%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 3-amino-4-fluorophenyl 3-methyl-2-pyridyl ketone(4.20 g, 0.171 mol), sodium thiocyanate (4.19 g, 0.0517 mol) and glacial acetic acid is added a solution of bromine in acetic acid (2M, 12 ml, 0.0240 mol) over a one hour period. The resultant mixture is stirred one hour at room temperature and poured into cold water. The precipitate is filtered and dried to afford the title compound as a green solid (5.43 g, >100%) which is identified by NMR and mass spectral analysis.

Workup

  1. filtrationThe precipitate is filtered
  2. customdried

Sources & evidence

ORD record
ord-19a20f7f68d44d88ab8d02b254a6f989
Source dataset
uspto-grants-2004_03
Patent number
US06706663B2

Linked notes

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