1-Propanol → HCID 131723497, compound

HRID 1281689Notes

Reaction equation

HRID 1281689 reaction equation
[C:1]([O:4][C@@H:5]1[CH2:10][CH2:9][CH2:8][C@@H:7]([NH:11][C:12]2[CH:17]=[C:16]([Cl:18])[C:15]([Cl:19])=[CH:14][C:13]=2[N+:20]([O-])=O)[C@@H:6]1[O:23][C:24](=[O:26])[CH3:25])(=[O:3])[CH3:2].[CH2:27](O)CC>[Ni]>[C:1]([O:4][C@@H:5]1[CH2:10][CH2:9][CH2:8][C@@H:7]([N:11]2[C:12]3[CH:17]=[C:16]([Cl:18])[C:15]([Cl:19])=[CH:14][C:13]=3[N:20]=[CH:27]2)[C@@H:6]1[O:23][C:24](=[O:26])[CH3:25])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 10311-PropanolHCID 131723498HCID 131723498, compound

Product 1

HCID 131723497HCID 131723497, compound

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

(±)-(1R*,2S*,3R*)-3-(4,5-Dichloro-2-nitroanilino)-1,2-cyclohexanediyl diacetate (part a of this example, 5.65 g, 13.9 mmol) in n-propanol (250 ml) was shaken with Raney nickel (Aldrich, ca. 0.50 g) under hydrogen (50 psi) for 2 h. Filtration through Celite and evaporation of solvent left the 5,6-diaminobenzimidazole intermediate. Triethylorthoformate (250 ml) and 4 drops of methanesulfonic acid were added and the solution stirred at room temperature for 2 days. Volatiles were evaporated in vacuo and the residual material chromatographed on silica gel. Title compound eluted with 2% methanol-ethyl acetate as off-white solid (1.87 g, 35%), m.p. 163-165° C. Anal. Calcd. for C17H18Cl2N2O4: C, 53.00; H, 4.71; N, 7.27; Cl, 18.41. Found: C, 52.85; H, 4.72; N, 7.17; Cl, 18.35.

Workup

  1. filtrationFiltration
  2. customthrough Celite and evaporation of solvent
  3. waitleft the 5,6-diaminobenzimidazole intermediate
  4. additionTriethylorthoformate (250 ml) and 4 drops of methanesulfonic acid were added
  5. customVolatiles were evaporated in vacuo
  6. customthe residual material chromatographed on silica gel
  7. washTitle compound eluted with 2% methanol-ethyl acetate as off-white solid (1.87 g, 35%), m.p. 163-165° C

Sources & evidence

ORD record
ord-566e89fd56ff4d589dcc549cea15f3ec
Source dataset
uspto-grants-2002_09
Patent number
US06455507B1

Reaction notes

Loading…