Water → HCID 9899528, compound

HRID 884408Notes

Reaction equation

HRID 884408 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([NH2:8])[CH:7]=1.[NH:12]1[CH2:17][CH2:16][S:15][CH2:14][CH2:13]1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[N+:9]([C:5]1[CH:4]=[CH:3][C:2]([N:12]2[CH2:17][CH2:16][S:15][CH2:14][CH2:13]2)=[CH:7][C:6]=1[NH2:8])([O-:11])=[O:10]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 67164ThiomorpholineHCID 742185-Chloro-2-nitroaniline

Product 1

HCID 9899528HCID 9899528, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 5-chloro-2-nitrophenylamine (2.5 g, 14 mmol), thiomorpholine (3.0 g, 30 mmol), and K2CO3 (2.0 g, 14 mmol) in DMF (20 mL) was stirred at 120° C. for 18 h. The reaction mixture was cooled to room temperature and poured into water (150 mL). The crude product that precipitated was collected by filtration, dried in vacuo, and purified by flash chromatography (silica gel, 4×15 cm, eluted with 20% ether in CHCl3) and recrystallized three times from methanol (MeOH) (0.49 g, 15%).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customThe crude product that precipitated
  3. filtrationwas collected by filtration
  4. customdried in vacuo
  5. custompurified by flash chromatography (silica gel, 4×15 cm, eluted with 20% ether in CHCl3)
  6. customrecrystallized three times from methanol (MeOH) (0.49 g, 15%)

Sources & evidence

ORD record
ord-5f3c6971423f4077a6e1cf977e7490d3
Source dataset
uspto-grants-2012_08
Patent number
US08242115B2

Reaction notes

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