Water → HCID 20293332, compound

HRID 1413092Notes

Reaction equation

HRID 1413092 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[NH:9][C:10]([C:12]1[CH:13]=[C:14]([C:16]([Cl:21])=[CH:17][C:18]=1[O:19][CH3:20])[NH2:15])=[O:11].C(N(CC)[C:25](Cl)=[S:26])C.ClC1C=CC=CC=1.O>C(Cl)Cl>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[NH:9][C:10]([C:12]1[CH:13]=[C:14]([N:15]=[C:25]=[S:26])[C:16]([Cl:21])=[CH:17][C:18]=1[O:19][CH3:20])=[O:11]

Participants

6

Reactant 4

HCID 962WaterHCID 7964ChlorobenzeneHCID 66607Diethylthiocarbamoyl chlorideHCID 20293324HCID 20293324, compound

Product 1

HCID 20293332HCID 20293332, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-[N-(2,6-dimethylphenyl)carbamoyl]-4-methoxy-6-chloroaniline (650 mg), diethylthiocarbamoyl chloride (360 mg) and chlorobenzene (6 ml) is refluxed for 30 minutes. The reaction mixture is mixed with water and shaken with methylene chloride. The organic layer is washed with water, dried over Glauber's salt and concentrated to remove the solvent. The residue is chromatographed on a column of silica gel, which is eluted with methylene chloride. The eluted fractions are collected and the solvent is evaporated. The residue is recrystallized from ethyl acetate to give 3-[N-(2,6-dimethylphenyl)carbamoyl]-4-methoxy-6-chlorophenyl isothiocyanate (340 mg) as crystals melting at 191°-192.5° C.

Workup

  1. temperatureis refluxed for 30 minutes
  2. washThe organic layer is washed with water
  3. dry with materialdried over Glauber's salt
  4. concentrationconcentrated
  5. customto remove the solvent
  6. customThe residue is chromatographed on a column of silica gel, which
  7. washis eluted with methylene chloride
  8. customThe eluted fractions are collected
  9. customthe solvent is evaporated
  10. customThe residue is recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-58ef4aadb95b413b9d335d6c8ad58ceb
Source dataset
uspto-grants-1981_02
Patent number
US04248869

Reaction notes

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