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

HRID 1398837Notes

Reaction equation

HRID 1398837 reaction equation
[NH2:1][C:2]1[C:3]([NH:13][CH2:14][CH2:15][CH2:16][OH:17])=[C:4]([CH:9]=[CH:10][C:11]=1[Cl:12])[C:5]([O:7][CH3:8])=[O:6].[Cl:18][C:19]1[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:20]=1[N:26]=[C:27]=[S:28]>O1CCCC1.[Na].[H][H].C(=O)([O-])[O-]>[Cl:12][C:11]1[CH:10]=[CH:9][C:4]([C:5]([O:7][CH3:8])=[O:6])=[C:3]([NH:13][CH2:14][CH2:15][CH2:16][OH:17])[C:2]=1[NH:1][C:27](=[S:28])[NH:26][C:20]1[CH:21]=[CH:22][C:23]([Cl:25])=[CH:24][C:19]=1[Cl:18]

Participants

6

Reactant 2

HCID 810662,4-Dichloro-1-isothiocyanatobenzeneHCID 68739849Methyl 3-amino-4-chloro-2-((3-hydroxypropyl)amino]benzoate

Product 1

HCID 86632879Methyl 4-chloro-3-{[(2,4-dichlorophenyl)carbamothioyl]amino}-2-[(3-hydroxypropyl)amino]benzoateYield 83.7%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 19660Carbonate IonSolventHCID 178506446HCID 178506446, compoundSolvent

Procedure

A mixture of methyl 3-amino-4-chloro-2-[(3-hydroxypropyl)amino]benzoate (13.1 g, 50.6 mmol) and 2,4-dichloro-1-isothiocyanatobenzene (13.4 g, 65.8 mmol) in tetrahydrofuran (150 mL) was stirred at room temperature for 3 days. The mixture was diluted with saturated aqueous sodium hydrogen, carbonate, concentrated in vacuo, 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 washed with diisopropyl ether to give methyl 4-chloro-3-{[(2,4-dichlorophenyl)carbamothioyl]amino}-2-[(3-hydroxypropyl)amino]benzoate as a colorless powder (19.6 g)

Workup

  1. concentrationconcentrated in vacuo
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. washThe residue was washed with diisopropyl ether

Sources & evidence

ORD record
ord-9846cb5f428e4597804d17ddcd8d4c40
Source dataset
uspto-grants-2014_12
Patent number
US08901141B2

Reaction notes

Loading…