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

HRID 1421477Notes

Reaction equation

HRID 1421477 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.C1(C)C=CC=CC=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

6

Reactant 4

HCID 1140TolueneHCID 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

Conditions

Temperature
80 °C

Procedure

5,6-Dichloro-1,2-phenylenediamine (0.61 g, 3.4 mmol), and isopropyl isothiocyanate (0.39 g, 3.8 mmol) were combined in anhydrous pyridine (10 mL) and were heated to 80° C. for 15 min. Dicyclohexylcarbodiimide (1.06 g, 5.14 mmol) was then added and the resulting mixture was allowed to stir at 100° C. for 5 h. Toluene (30 mL) was added and the mixture was concentrated by rotary evaporation leaving a brown residue. The product was further purified by silica gel chromatography using 6.5:3:0.5 ethyl acetate/hexane/triethylamine to afford a gummy solid which was recrystallised from acetonitrile to give 0.46 g (60%) of a tan solid; m.p. 218-220° C. Anal. Calcd for C10H11Cl2N3 : C, 49.20; H, 4.54; N, 17.21. Found: C, 49.31; H, 4.59; N, 17.33.

Workup

  1. concentrationthe mixture was concentrated by rotary evaporation
  2. customleaving a brown residue
  3. customThe product was further purified by silica gel chromatography
  4. customto afford a gummy solid which
  5. customwas recrystallised from acetonitrile

Sources & evidence

ORD record
ord-eeb288fd697d4b41b3ea17f4d83b6144
Source dataset
uspto-grants-2000_06
Patent number
US06077832

Reaction notes

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