Water → HCID 20293305, compound

HRID 903555Notes

Reaction equation

HRID 903555 reaction equation
[CH3:1][N:2]([CH3:17])[C:3]([C:5]1[CH:6]=[C:7]([N+:14]([O-:16])=[O:15])[CH:8]=[C:9]([CH3:13])[C:10]=1[O:11][CH3:12])=O.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:19].O.CCOCC>C1C=CC=CC=1>[CH3:1][N:2]([CH3:17])[C:3]([C:5]1[CH:6]=[C:7]([N+:14]([O-:16])=[O:15])[CH:8]=[C:9]([CH3:13])[C:10]=1[O:11][CH3:12])=[S:19]

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 14817Phosphorus sulfide (P2S5)HCID 20293311HCID 20293311, compound

Product 1

HCID 20293305HCID 20293305, compoundYield 85.2%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 3-dimethylcarbamoyl-4-methoxy-5-methylnitrobenzene (1.10 g) in benzene (11 ml) is added phosphorus pentasulfide (3.08 g), and the resultant mixture is refluxed for 1 hour. After sooling, the reaction mixture is mixed with icy water and shaken with ether. The organic layer is washed with water, dried over Glauber's salt and concentrated under reduced pressure to remove the solvent. The residue is chromatographed on a column of silica gel, which is eluted with benzene, methylene chloride and then methylene chloride/2% methanol in order. The eluted fractions are concentrated under reduced pressure and the residue is washed with isopropyl ether to give 3-dimethylthiocarbamoyl-4-methoxy-5-methyl-nitrobenzene (1.0 g) as crystals melting at 138°-139° C.

Workup

  1. washThe organic layer is washed with water
  2. dry with materialdried over Glauber's salt
  3. concentrationconcentrated under reduced pressure
  4. customto remove the solvent
  5. customThe residue is chromatographed on a column of silica gel, which
  6. washis eluted with benzene, methylene chloride
  7. concentrationThe eluted fractions are concentrated under reduced pressure
  8. washthe residue is washed with isopropyl ether

Sources & evidence

ORD record
ord-b2b5b08efaae4d99a410f0e256ea3ddf
Source dataset
uspto-grants-1980_10
Patent number
US04228165

Reaction notes

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