Lawesson's reagent → 4-Morpholinobenzenecarbothioamide

HRID 56115

Reaction equation

HRID 56115 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:15]=[CH:14][C:10]([C:11]([NH2:13])=O)=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:25])=CC=1>C1COCC1>[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:15]=[CH:14][C:10]([C:11](=[S:25])[NH2:13])=[CH:9][CH:8]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 221422424-(Morpholin-4-yl)benzamide

Product 1

HCID 27953604-MorpholinobenzenecarbothioamideYield 83.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 4-morpholinobenzamide (4.91 g, 23.80 mmol) in THF (70 mL) was added Lawesson's Reagent (10.60 g, 26.20 mmol) with stirring. The mixture was heated at 70° C. for 4 h, then cooled to rt and concentrated in vacuo. CH2Cl2 (30 mL) and water (100 mL) was added to the residue. The mixture was then filtered and the filter cake was washed with water and dried to give the title compound as a yellow solid (4.41 g, 83.3%).

Workup

  1. temperaturecooled to rt
  2. concentrationconcentrated in vacuo
  3. additionCH2Cl2 (30 mL) and water (100 mL) was added to the residue
  4. filtrationThe mixture was then filtered
  5. washthe filter cake was washed with water
  6. customdried

Sources & evidence

ORD record
ord-b3263675a8b3462c97d4844f0524773b
Source dataset
uspto-grants-2016_09
Patent number
US09434695B2

Linked notes

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