4-chloro-1-isothiocyanato-2-(trifluoromethyl)benzene → HCID 86632930, compound

HRID 1628704Notes

Reaction equation

HRID 1628704 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]=[CH:23][C:22]([N:25]=[C:26]=[S:27])=[C:21]([C:28]([F:31])([F:30])[F:29])[CH:20]=1>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][CH2:16][OH:17])[C:2]=1[NH:1][C:26](=[S:27])[NH:25][C:22]1[CH:23]=[CH:24][C:19]([Cl:18])=[CH:20][C:21]=1[C:28]([F:29])([F:30])[F:31]

Participants

4

Reactant 2

HCID 27366894-chloro-1-isothiocyanato-2-(trifluoromethyl)benzeneHCID 68739849Methyl 3-amino-4-chloro-2-((3-hydroxypropyl)amino]benzoate

Product 1

HCID 86632930HCID 86632930, compoundYield 91.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 3-amino-4-chloro-2-[(3-hydroxypropyl)amino]benzoate (12.5 g, 48.3 mmol) and 4-chloro-1-isothiocyanato-2-(trifluoromethyl)benzene (14.9 g, 62.8 mmol) in tetrahydrofuran (150 mL) was stirred at room temperature for 2 days. The mixture was concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with ethyl acetate. The filtrate was concentrated in vacuo to give methyl 4-chloro-3-({[4-chloro-2-(trifluoromethyl)phenyl]carbamothioyl}amino)-2-[(3-hydroxypropyl)amino]benzoate as a brown oil (22.0 g)

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customThe residue was purified by flash column chromatography on silica gel eluting with ethyl acetate
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-edf8d651186048fb9fe2543ccc94ee6f
Source dataset
uspto-grants-2014_07
Patent number
US08785460B2

Reaction notes

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