1-Cyclohexyl-3-(2-morpholinoethyl)carbodiimide metho-p-toluenesulfonate → 5,6-dichloro-N-isopropyl-1H-benzo[d]imidazol-2-amine

HRID 1421478Notes

Reaction equation

HRID 1421478 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.CC1C=CC(S([O-])(=O)=O)=CC=1.C[N+]1(CC[N:37]=[C:38]=[N:39][CH:40]2[CH2:45]CCC[CH2:41]2)CCOCC1>N1C=CC=CC=1>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]2[NH:10][C:38]([NH:39][CH:40]([CH3:45])[CH3:41])=[N:37][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 172201-Cyclohexyl-3-(2-morpholinoethyl)carbodiimide metho-p-toluenesulfonateHCID 75263Isopropyl IsothiocyanateHCID 108450203,4-Dichlorobenzene-1,2-diamine

Product 1

HCID 229954185,6-dichloro-N-isopropyl-1H-benzo[d]imidazol-2-amineYield 67%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

5,6-Dichloro-1,2-phenylenediamine (200.0 g, 1.13 mol), isopropyl isothiocyanate (122.0 g, 1.21 mol), 1-cyclohexyl-3-(2-morpholinoethyl)carbodiimide metho-p-toluenesulfonate (622.0 g, 1.47 mol) and pyridine (4 L) were used according to general procedure I. The product was recrystallized from acetonitrile to give 184 g (67%) of a brown solid. Analytical data were consistent with those reported above.

Workup

  1. customThe product was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-909198bee7384d6e9d2c69d7b1e7d3b6
Source dataset
uspto-grants-2000_06
Patent number
US06077832

Reaction notes

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