HCID 68737846, compound → HCID 68908486, compound

HRID 1628537Notes

Reaction equation

HRID 1628537 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[CH:25]=[C:24]([O:26]C)C=C[C:21]=1[N:28]=C=S>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][NH:28][CH2:21][CH:20]([Cl:19])[CH2:25][CH2:24][OH:26]

Participants

4

Reactant 2

HCID 68737846HCID 68737846, compoundHCID 82491428HCID 82491428, compound

Product 1

HCID 68908486HCID 68908486, compoundYield 45.3%

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 2-chloro-1-isothiocyanato-4-methoxybenzene (2.94 g, 14.7 mmol) in tetrahydrofuran (20 mL) was stirred for 36 h at 70° C. The reaction mixture was concentrated in vacuo and purified by flash column chromatography on silica gel eluting with a 50% ethyl acetate/n-hexane mixture to give the title compound as a pale yellow oil (1.57 g, 3.32 mmol, 45%).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. custompurified by flash column chromatography on silica gel eluting with a 50% ethyl acetate/n-hexane mixture

Sources & evidence

ORD record
ord-a476709f9b6646e086c310204d48e664
Source dataset
uspto-grants-2014_07
Patent number
US08785460B2

Reaction notes

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