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

HRID 1628567Notes

Reaction equation

HRID 1628567 reaction equation
[NH2:1][C:2]1[C:3]([NH:13][CH2:14][CH2:15][OH:16])=[C:4]([CH:9]=[CH:10][C:11]=1[Cl:12])[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: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][OH:16])[C:2]=1[NH:1][C:26](=[S:27])[NH:25][C:19]1[CH:20]=[CH:21][C:22]([Cl:24])=[CH:23][C:18]=1[Cl:17]

Participants

4

Reactant 2

HCID 810662,4-Dichloro-1-isothiocyanatobenzeneHCID 68738315Methyl 3-amino-4-chloro-2-[(2-hydroxyethyl)amino]benzoate

Product 1

HCID 86632917Methyl 4-chloro-3-{[(2,4-dichlorophenyl)carbamothioyl]amino}2-[(2-hydroxyethyl)amino]benzoateYield 48.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 3-amino-4-chloro-2-[(2-hydroxyethyl)amino]benzoate (1.068 g, 3.16 mmol) and 2,4-dichlorophenylisothiocyanate (0.86 g, 4.21 mmol) in tetrahydrofuran (40 mL) was stirred at 50° C. for 14 hr. The reaction mixture was concentrated in vacuo. The residue was purified by flash chromatography on silica gel eluting with a 25-70% ethyl acetate/n-hexane gradient mixture and flash chromatography on NH-silica gel eluting with a 50-100% ethyl acetate/n-hexane gradient mixture to give the title compound (686.9 mg, 1.53 mmol, 48%) as a pale orange amorphous.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customThe residue was purified by flash chromatography on silica gel eluting with a 25-70% ethyl acetate/n-hexane gradient mixture and flash chromatography on NH-silica gel eluting with a 50-100% ethyl acetate/n-hexane gradient mixture

Sources & evidence

ORD record
ord-839ec5d4326f45e2b6517ae1fc7ef222
Source dataset
uspto-grants-2014_07
Patent number
US08785460B2

Reaction notes

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