Toluene → HCID 68276383, compound

HRID 334402Notes

Reaction equation

HRID 334402 reaction equation
[NH2:1][C:2]1[C:3]([C:18]([NH2:20])=O)=[N:4][C:5]([S:8][CH2:9][C:10]2[CH:15]=[C:14]([F:16])[CH:13]=[C:12]([F:17])[CH:11]=2)=[CH:6][CH:7]=1.C1(C)C=CC=CC=1>C(OCC)(=O)C>[NH2:1][C:2]1[C:3]([C:18]#[N:20])=[N:4][C:5]([S:8][CH2:9][C:10]2[CH:15]=[C:14]([F:16])[CH:13]=[C:12]([F:17])[CH:11]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 1140TolueneHCID 68276473HCID 68276473, compound

Product 1

HCID 68276383HCID 68276383, compoundYield 106.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 3-amino-6-(3,5-difluorobenzylthio)picolinoamide (2.37 mmol, 0.7 g) and P2Cl5 (9.48 mmol, 1.346 g), 20 ml of toluene and 1 ml of ionic solvent (1-butyl-3-methylimidazolium tetrafluoroborate) are placed in a microwave reactor and then heated at 140° C. for 30 minutes. The crude reaction product is then concentrated under reduced pressure and the orange crystals thus obtained are redissolved in ethyl acetate and washed using saturated aqueous NaHCO3 solution. The organic phase is dried on magnesium sulfate and then concentrated to yield 0.7 g of a brown oil. This crude reaction product is purified by silica gel chromatography (AcOEt/heptane+0.1% of NEt3) to yield, after concentration, 0.15 g (23%) of orange crystals.

Workup

  1. customare placed in a microwave reactor
  2. customThe crude reaction product
  3. concentrationis then concentrated under reduced pressure
  4. customthe orange crystals thus obtained
  5. washwashed
  6. customThe organic phase is dried on magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-9dc689210e464efc9a353a163df85984
Source dataset
uspto-grants-2014_11
Patent number
US08883821B2

Reaction notes

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