3,5-Dichlorophenyl isothiocyanate → HCID 54453882, compound

HRID 1859710Notes

Reaction equation

HRID 1859710 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][C:17]=1[O:18][CH3:19])[C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=1)=[O:6].[Cl:20][C:21]1[CH:22]=[C:23]([N:28]=[C:29]=[S:30])[CH:24]=[C:25]([Cl:27])[CH:26]=1>C(Cl)Cl>[Cl:20][C:21]1[CH:22]=[C:23]([NH:28][C:29](=[S:30])[NH:1][C:2]2[CH:3]=[C:4]([CH:15]=[CH:16][C:17]=2[O:18][CH3:19])[C:5]([NH:7][C:8]2[CH:9]=[CH:10][C:11]([CH3:14])=[CH:12][CH:13]=2)=[O:6])[CH:24]=[C:25]([Cl:27])[CH:26]=1

Participants

4

Reactant 2

HCID 1387763,5-Dichlorophenyl isothiocyanateHCID 16788996HCID 16788996, compound

Product 1

HCID 54453882HCID 54453882, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of 3-amino-4-methoxy-N-p-tolyl-benzamide from Example 7 (0.515 g, 2.01 mmol) in methylene chloride (75 mL) was heated to the boiling point, then 3,5-dichlorophenyl isothiocyanate (0.411 g, 2.01 mmol) was added, and the reaction was allowed to stand at room temperature. After 2 days, the mixture was stripped of solvent at 40° C. and the residue triturated in warm methylene chloride. The solid was filtered off, redissolved in methylene chloride/methanol, and filtered to clarity. Evaporation of the solvent afforded the product (0.305 g); m.p. 178-180° C.

Workup

  1. temperaturewas heated to the boiling point
  2. customto stand at room temperature
  3. customwas stripped of solvent at 40° C.
  4. customthe residue triturated in warm methylene chloride
  5. filtrationThe solid was filtered off
  6. dissolutionredissolved in methylene chloride/methanol
  7. filtrationfiltered to clarity
  8. customEvaporation of the solvent

Sources & evidence

ORD record
ord-ef365f5632e042e19176b0372c4f6673
Source dataset
uspto-grants-2003_03
Patent number
US06528528B2

Reaction notes

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