Tetrahydrofuran → 2-Methoxybenzene-1-carbothioamide

HRID 1616634Notes

Reaction equation

HRID 1616634 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[CH:8][C:4]=1[C:5]([NH2:7])=O.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:13].C1COCC1>>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[CH:8][C:4]=1[C:5]([NH2:7])=[S:13]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 14817Phosphorus sulfide (P2S5)HCID 755402-Methoxybenzamide

Product 1

HCID 27597312-Methoxybenzene-1-carbothioamideYield 185.7%

Procedure

Combine 2-methoxy benzamide (10.0 g, 66.2 mmol) with phosphorus pentasulfide (10.1 g, 22.7 mmol) and THF (200 mmol) in a sealed vessel and stir for 30 minutes at room temperature. Sonicate the mixture for 1 hour and then allow the mixture to stand at room temperature. Decant the THF solution from the solids and concentrate. Chromatograph the resulting residue over silica gel (MeOH/CH2Cl2) to give 2-methoxy-thiobenzamide (7.05 g, 64%).

Workup

  1. customSonicate the mixture for 1 hour
  2. customto stand at room temperature
  3. customDecant the THF solution from the solids
  4. concentrationconcentrate

Sources & evidence

ORD record
ord-14ce07f1aa674dd4bd62f3bd8b546bc8
Source dataset
uspto-grants-2014_07
Patent number
US08765796B2

Reaction notes

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