2,4-Dichloro-1-isothiocyanatobenzene → HCID 86632877, compound

HRID 1628478Notes

Reaction equation

HRID 1628478 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][CH2:12][CH2:13][CH2:14][OH:15].[Cl:16][C:17]1[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:18]=1[N:24]=[C:25]=[S:26]>O1CCCC1>[NH2:1][C:2]1[C:3]([NH:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][OH:15])=[C:4]([NH:8][C:25]([NH:24][C:18]2[CH:19]=[CH:20][C:21]([Cl:23])=[CH:22][C:17]=2[Cl:16])=[S:26])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 810662,4-Dichloro-1-isothiocyanatobenzeneHCID 68735878HCID 68735878, compound

Product 1

HCID 86632877HCID 86632877, compoundYield 32.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 5-[(2,6-diaminophenyl)amino]pentan-1-ol (Reference Example 110; 873 mg, 4.17 mmol) in tetrahydrofuran (30 mL) was added a solution of 2,4-dichlorophenyl isothiocyanate (936 mg, 4.59 mmol) in tetrahydrofuran (10 mL) at 0° C. The resultant mixture was stirred at 0° C. for 2 hr and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with a 50-90% ethyl acetate/n-hexane gradient mixture to give the title compound as an oil (554 mg, 1.34 mmol, 32%).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by flash column chromatography on silica gel eluting with a 50-90% ethyl acetate/n-hexane gradient mixture

Sources & evidence

ORD record
ord-2e50dd796e4c4d6293c661c718592f00
Source dataset
uspto-grants-2014_07
Patent number
US08785460B2

Reaction notes

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