3,5-Dichloro-2-isothiocyanatopyridine → HCID 86632902, compound

HRID 1628533Notes

Reaction equation

HRID 1628533 reaction equation
[NH2:1][C:2]1[C:3]([NH:13][CH2:14][CH2:15][CH2:16][CH2:17][OH:18])=[C:4]([CH:9]=[CH:10][C:11]=1[Cl:12])[C:5]([O:7][CH3:8])=[O:6].[Cl:19][C:20]1[C:21]([N:27]=[C:28]=[S:29])=[N:22][CH:23]=[C:24]([Cl:26])[CH:25]=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][CH2:17][OH:18])[C:2]=1[NH:1][C:28](=[S:29])[NH:27][C:21]1[C:20]([Cl:19])=[CH:25][C:24]([Cl:26])=[CH:23][N:22]=1

Participants

4

Reactant 2

HCID 233404453,5-Dichloro-2-isothiocyanatopyridineHCID 68737846HCID 68737846, compound

Product 1

HCID 86632902HCID 86632902, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 3-amino-4-chloro-2-[(4-hydroxybutyl)amino]benzoate (2.00 g, 7.33 mmol) and 3,5-dichloro-2-isothiocyanatopyridine (1.80 g, 8.80 mmol) in tetrahydrofuran (20 mL) was stirred for 12 h at room temperature. The reaction mixture was concentrated in vacuo and purified by flash column chromatography on NH-silica gel eluting with a 10-80% ethyl acetate/n-hexane gradient mixture to give the title compound as a colorless solid (2.76 g, 5.78 mmol, 79%).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. custompurified by flash column chromatography on NH-silica gel eluting with a 10-80% ethyl acetate/n-hexane gradient mixture

Sources & evidence

ORD record
ord-af918c6e93814591980c3cf369adce9e
Source dataset
uspto-grants-2014_07
Patent number
US08785460B2

Reaction notes

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