Phosphorus sulfide (P2S5) → Benzenecarbothioamide, 4-(diethylamino)-

HRID 56109Notes

Reaction equation

HRID 56109 reaction equation
[CH2:1]([N:3]([CH2:13][CH3:14])[C:4]1[CH:12]=[CH:11][C:7]([C:8]([NH2:10])=O)=[CH:6][CH:5]=1)[CH3:2].P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:16]>C1COCC1>[CH2:1]([N:3]([CH2:13][CH3:14])[C:4]1[CH:12]=[CH:11][C:7]([C:8](=[S:16])[NH2:10])=[CH:6][CH:5]=1)[CH3:2]

Participants

4

Reactant 2

HCID 14817Phosphorus sulfide (P2S5)HCID 193536744-(Diethylamino)benzamide

Product 1

HCID 28410527Benzenecarbothioamide, 4-(diethylamino)-Yield 20.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of 4-(diethylamino)benzamide (5.66 g, 29.43 mmol) in THF (80 mL) was added P2S5 (9.81 g, 44.14 mmol) at 50° C. over a period of 1 h. The mixture was heated at 55° C. for 8 h, then cooled to rt, filtered and the filtrate was concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=2:1) to give the title compound as a yellow solid (1.23 g, 20%).

Workup

  1. temperaturecooled to rt
  2. filtrationfiltered
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=2:1)

Sources & evidence

ORD record
ord-6d14eed077b7449f9c742e1b9f77be85
Source dataset
uspto-grants-2016_09
Patent number
US09434695B2

Reaction notes

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