Tetrahydrofuran → Methyl 3-{[(2,4-dichloro-6-methylphenyl)carbamothioyl]amino}-2-[(2-hydroxyethyl)amino]benzoate

HRID 1398923Notes

Reaction equation

HRID 1398923 reaction equation
[NH2:1][C:2]1[C:3]([NH:11][CH2:12][CH2:13][OH:14])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([O-:7])=[O:6].[Cl:15][C:16]1[CH:21]=[C:20]([Cl:22])[CH:19]=[C:18]([CH3:23])[C:17]=1[N:24]=[C:25]=[S:26].O1CCC[CH2:28]1>>[Cl:15][C:16]1[CH:21]=[C:20]([Cl:22])[CH:19]=[C:18]([CH3:23])[C:17]=1[NH:24][C:25]([NH:1][C:2]1[C:3]([NH:11][CH2:12][CH2:13][OH:14])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([O:7][CH3:28])=[O:6])=[S:26]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 27360131,5-Dichloro-2-isothiocyanato-3-methylbenzeneHCID 866329163-Amino-2-[(2-hydroxyethyl)amino]benzoate

Product 1

HCID 86632915Methyl 3-{[(2,4-dichloro-6-methylphenyl)carbamothioyl]amino}-2-[(2-hydroxyethyl)amino]benzoate

Conditions

Temperature
50 °C

Procedure

A solution of 3-amino-2-[(2-hydroxyethyl)amino]benzoate (521 mg, 2.48 mmol) and 2,4-dichloro-6-methylphenylisothiocyanate (595 mg, 2.73 mmol) in tetrahydrofuran (25 mL) was stirred at room temperature for 18 hr. The mixture was warmed to 50° C. and it was stirred at 50° C. for 24 hr. The reaction mixture was concentrated in vacuo. The residue was purified by flash chromatography on silica gel eluting with a 20-80% ethyl acetate/n-hexane gradient mixture to give the title compound (959.9 mg) as a colorless amorphous.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customThe residue was purified by flash chromatography on silica gel eluting with a 20-80% ethyl acetate/n-hexane gradient mixture

Sources & evidence

ORD record
ord-59338fce01924d7e939a28c978a152e6
Source dataset
uspto-grants-2014_12
Patent number
US08901141B2

Reaction notes

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