Carbon Disulfide → HCID 20293330, compound

HRID 1413091Notes

Reaction equation

HRID 1413091 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]([CH3:13])[C:10]([NH2:14])=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6].C(N(CC)CC)C.C(Cl)(=O)OCC.[OH-].[Na+].[C:30](=S)=[S:31]>O1CCCC1.O.C(Cl)Cl>[CH3:8][O:7][C:5]([C:4]1[CH:9]=[C:10]([N:14]=[C:30]=[S:31])[C:11]([CH3:13])=[CH:12][C:3]=1[O:2][CH3:1])=[O:6]

Participants

9

Reactant 5

HCID 6348Carbon DisulfideHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 14798Sodium HydroxideHCID 20293331HCID 20293331, compound

Product 1

HCID 20293330HCID 20293330, compoundYield 80.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2-methoxy-4-methyl-5-aminobenzoate (975 mg) in tetrahydrofuran (5 ml) are added triethylamine (1.52 g) and carbon disulfide (1.14 g), and the resultant mixture is stirred at room temperature for 2.5 hours. Ethyl chlorocarbonate (1.63 g) is added to the mixture, which is stirred for additional 20 minutes at room temperature. A solution of sodium hydroxide (1.2 g) in water (32 ml) is added to the mixture, which is stirred for 15 minutes. The reaction mixture is mixed with an excess amount of water and shaken with methylene chloride. The organic layer is dried over Glauber's salt and the solvent is evaporated. The residue is dissolved in methylene chloride and chromatographed on a column of silica gel. Evaporating the solvent from the elution, the residue is dissolved in isopropyl ether and n-hexane is added thereto. The precipitated crystals are filtered to give 3-methoxycarbonyl-4-methoxy-6-methylphenyl isothiocyanate (952 mg) as crystals melting at 86°-87.5° C.

Workup

  1. stirringis stirred for 15 minutes
  2. dry with materialThe organic layer is dried over Glauber's salt
  3. customthe solvent is evaporated
  4. dissolutionThe residue is dissolved in methylene chloride
  5. customchromatographed on a column of silica gel
  6. customEvaporating the solvent
  7. washfrom the elution
  8. dissolutionthe residue is dissolved in isopropyl ether
  9. additionn-hexane is added
  10. filtrationThe precipitated crystals are filtered

Sources & evidence

ORD record
ord-0aef296270324a7dbb21a5dd8c78da91
Source dataset
uspto-grants-1981_02
Patent number
US04248869

Reaction notes

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