Naphthalene-2-carboxamide → naphthalene-2-carbothioamide

HRID 1421927Notes

Reaction equation

HRID 1421927 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]([NH2:13])=O.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:23])=CC=1>O1CCCC1>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11](=[S:23])[NH2:13]

Participants

4

Reactant 2

HCID 75245Naphthalene-2-carboxamideHCID 87949Lawesson's reagent

Product 1

HCID 2800333naphthalene-2-carbothioamideYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the above amide (10.0 g, 58 mmol) in dry tetrahydrofuran (250 ml) was added [2,4-bis-(4-methoxyphenyl)-1,3-dithia-2,4-diphosphenate-2,4-disulfide] (Lawesson's reagent) (16.5 g, 41 mmol) and the resulting mixture was stirred at room temperature for 48 h. The volatiles were evaporated in vacuo and the residue was dissolved in ethyl acetate (100 ml) and filtered through silicagel (100 ml) using ethyl acetate as eluent. The solvent was evaporated in vacuo and to the residue was added a mixture of ethyl acetate (25 ml) and heptane (25 ml). The precipitate was filtered off and washed with heptane (40 ml), dried in vacuo at 50° C. which afforded 9.0 g (83%) of naphthalene-2-carbothioic acid amide as a solid.

Workup

  1. customThe volatiles were evaporated in vacuo
  2. dissolutionthe residue was dissolved in ethyl acetate (100 ml)
  3. filtrationfiltered through silicagel (100 ml)
  4. customThe solvent was evaporated in vacuo and to the residue
  5. additionwas added
  6. additiona mixture of ethyl acetate (25 ml) and heptane (25 ml)
  7. filtrationThe precipitate was filtered off
  8. washwashed with heptane (40 ml)
  9. customdried in vacuo at 50° C. which

Sources & evidence

ORD record
ord-bfd94410e0064900a18913932bb41e3e
Source dataset
uspto-grants-2000_06
Patent number
US06080770

Reaction notes

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