2,4-Dichloro-1-isothiocyanatobenzene → Methyl 3-({[(2,4-dichlorophenyl)amino]carbonothioyl}amino)-2-[(3-hydroxypropyl)amino]benzoate

HRID 1628469Notes

Reaction equation

HRID 1628469 reaction equation
[NH2:1][C:2]1[C:3]([NH:12][CH2:13][CH2:14][CH2:15][OH:16])=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[Cl:17][C:18]1[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:19]=1[N:25]=[C:26]=[S:27]>O1CCCC1>[Cl:17][C:18]1[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:19]=1[NH:25][C:26]([NH:1][C:2]1[C:3]([NH:12][CH2:13][CH2:14][CH2:15][OH:16])=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6])=[S:27]

Participants

4

Reactant 2

HCID 810662,4-Dichloro-1-isothiocyanatobenzeneHCID 68736607Methyl 3-amino-2-[(3-hydroxypropyl)amino]benzoate

Product 1

HCID 86632874Methyl 3-({[(2,4-dichlorophenyl)amino]carbonothioyl}amino)-2-[(3-hydroxypropyl)amino]benzoateYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 3-amino-2-[(3-hydroxypropyl)amino]benzoate (1.00 g, 4.46 mmol) in tetrahydrofuran (12 mL) was added 2,4-dichlorophenyl isothiocyanate (910 mg, 4.46 mmol), and the mixture was stirred at room temperature for 3 hr. The mixture was concentrated and the residue was diluted with saturated aqueous sodium hydrogen carbonate, and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with a 10-50% ethyl acetate/n-hexane gradient mixture. The filtrate was concentrated in vacuo to give the title compound as a brown solid (1.87 g, 4.37 mmol, 98%).

Workup

  1. concentrationThe mixture was concentrated
  2. additionthe residue was diluted with saturated aqueous sodium hydrogen carbonate
  3. extractionextracted with ethyl acetate
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash column chromatography on silica gel eluting with a 10-50% ethyl acetate/n-hexane gradient mixture
  9. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-635c107a65ae44e283951cb9cc995c3d
Source dataset
uspto-grants-2014_07
Patent number
US08785460B2

Reaction notes

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