2,4-Dichloro-1-isothiocyanatobenzene → Methyl 4-{[2-amino-6-({[(2,4-dichlorophenyl)amino]carbonothioyl}amino)phenyl]amino}-3-hydroxybutanoate

HRID 1628449Notes

Reaction equation

HRID 1628449 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([NH2:8])[C:3]=1[NH:9][CH2:10][CH:11]([OH:17])[CH2:12][C:13]([O:15][CH3:16])=[O:14].[Cl:18][C:19]1[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:20]=1[N:26]=[C:27]=[S:28]>O1CCCC1>[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([NH:8][C:27]([NH:26][C:20]2[CH:21]=[CH:22][C:23]([Cl:25])=[CH:24][C:19]=2[Cl:18])=[S:28])[C:3]=1[NH:9][CH2:10][CH:11]([OH:17])[CH2:12][C:13]([O:15][CH3:16])=[O:14]

Participants

4

Reactant 2

HCID 810662,4-Dichloro-1-isothiocyanatobenzeneHCID 68737495Methyl 4-[(2,6-diaminophenyl)amino]-3-hydroxybutanoate

Product 1

HCID 86632869Methyl 4-{[2-amino-6-({[(2,4-dichlorophenyl)amino]carbonothioyl}amino)phenyl]amino}-3-hydroxybutanoateYield 34%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of methyl 4-[(2,6-diaminophenyl)amino]-3-hydroxybutanoate (Reference Example 80; 100 mg, 0.418 mmol) in tetrahydrofuran (2 mL) was added a solution of 2,4-dichlorophenyl isothiocyanate (93.8 mg, 0.460 mmol) in tetrahydrofuran (2 mL) at 0° C. The resultant mixture was stirred at 0° C. for 1 hr and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with a 50-70% ethyl acetate/n-hexane gradient to give the title compound as an oil (62.5 mg, 0.141 mmol, 34%).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by flash column chromatography on silica gel eluting with a 50-70% ethyl acetate/n-hexane gradient

Sources & evidence

ORD record
ord-0a1328cbcf6c42169da99f73f34866e3
Source dataset
uspto-grants-2014_07
Patent number
US08785460B2

Reaction notes

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