2,4-Dichloro-1-isothiocyanatobenzene → HCID 86632864, compound

HRID 1398752Notes

Reaction equation

HRID 1398752 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([NH2:8])[C:3]=1[NH:9][CH2:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13].[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>[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([NH:8][C:26]([NH:25][C:19]2[CH:20]=[CH:21][C:22]([Cl:24])=[CH:23][C:18]=2[Cl:17])=[S:27])[C:3]=1[NH:9][CH2:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

4

Reactant 2

HCID 810662,4-Dichloro-1-isothiocyanatobenzeneHCID 68737549HCID 68737549, compound

Product 1

HCID 86632864HCID 86632864, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl N-(2,6-diaminophenyl)-beta-alaninate (Reference Example 25; 500 mg, 2.24 mmol) in tetrahydrofuran (22 mL) was added 2,4-dichlorophenyl isothiocyanate (503 mg, 2.46 mmol) at room temperature. The resultant mixture was stirred at room temperature for 1 hr and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with a 10-40% ethyl acetate/n-hexane gradient mixture and NH-silica gel eluting with a 10-90% ethyl acetate/n-hexane gradient mixture to give the title compound as a solid (533 mg, 1.25 mmol, 56%).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by flash column chromatography on silica gel eluting with a 10-40% ethyl acetate/n-hexane gradient mixture and NH-silica gel eluting with a 10-90% ethyl acetate/n-hexane gradient mixture

Sources & evidence

ORD record
ord-b1147e2219d04508834dd02f59e38aeb
Source dataset
uspto-grants-2014_12
Patent number
US08901141B2

Reaction notes

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