Dicyclohexylcarbodiimide → 5,6-dichloro-N-isopropyl-1H-benzo[d]imidazol-2-amine

HRID 2227168Notes

Reaction equation

HRID 2227168 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH2:10])=[C:6](N)[C:7]=1[Cl:8].C(N=C=S)(C)C.[CH:17]1([N:23]=[C:24]=[N:25]C2CCCCC2)[CH2:22]CCC[CH2:18]1>N1C=CC=CC=1>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]2[NH:10][C:24]([NH:23][CH:17]([CH3:22])[CH3:18])=[N:25][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 75263Isopropyl IsothiocyanateHCID 108450203,4-Dichlorobenzene-1,2-diamine

Product 1

HCID 229954185,6-dichloro-N-isopropyl-1H-benzo[d]imidazol-2-amineYield 60%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

5,6-Dichloro-1,2-phenylenediamine (0.61 g, 3.4 mmol), isopropyl isothiocyanate (0.39 g, 3.8 mmol), dicyclohexyl carbodiimide (1.06 g, 5.14 mmol) and pyridine (10 L) were used according to general procedure I. The product was recrystallized from acetonitrile to afford a tan solid (0.46 g, 60%); m.p. 218-220° C.

Workup

  1. customThe product was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-12e3f2f617e447bbb608f1b7f31318b7
Source dataset
uspto-grants-2002_07
Patent number
US06413938B1

Reaction notes

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