2,6-Dichloro-4-morpholin-4-YL-benzaldehyde → 6-[5-(4-Chloro-phenyl)-[1,3,4]oxadiazol-2-yl]-2-(2,6-dichloro-4-morpholin-4-yl-phenyl)-1H-benzoimidazole

HRID 1360740Notes

Reaction equation

HRID 1360740 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][C:11]([C:13]3[CH:14]=[C:15]([NH2:20])[C:16]([NH2:19])=[CH:17][CH:18]=3)=[N:10][N:9]=2)=[CH:4][CH:3]=1.[Cl:21][C:22]1[CH:29]=[C:28]([N:30]2[CH2:35][CH2:34][O:33][CH2:32][CH2:31]2)[CH:27]=[C:26]([Cl:36])[C:23]=1[CH:24]=O>CS(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:12][C:11]([C:13]3[CH:18]=[CH:17][C:16]4[N:19]=[C:24]([C:23]5[C:22]([Cl:21])=[CH:29][C:28]([N:30]6[CH2:31][CH2:32][O:33][CH2:34][CH2:35]6)=[CH:27][C:26]=5[Cl:36])[NH:20][C:15]=4[CH:14]=3)=[N:10][N:9]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 71486052,6-Dichloro-4-morpholin-4-YL-benzaldehydeHCID 669664354-[5-(4-Chloro-phenyl)-[1,3,4]oxadiazol-2-yl]-benzene-1,2-diamine

Product 1

HCID 252359016-[5-(4-Chloro-phenyl)-[1,3,4]oxadiazol-2-yl]-2-(2,6-dichloro-4-morpholin-4-yl-phenyl)-1H-benzoimidazole

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a 50 ml rbf was added 0.2250 g (0.785 mmol) 4-[5-(4-Chloro-phenyl)-[1,3,4]oxadiazol-2-yl]-benzene-1,2-diamine, 0.2041 g (0.785 mmol) of 2,6-Dichloro-4-morpholin-4-yl-benzaldehyde, and 5 mL of DMSO. To this dark brown solution was added 0.0190 g (0.118 mmol) of FeCl3. It was allowed to stir open to air for 18 h. The crude was then extracted with EtOAc, and the combined extracts were washed with water, brine and dried with Na2SO4. The volatiles were removed in vacuo and the concentrate was purified on silica gel (ACN/DCM, 1:9 to 10:0) to give the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 3.30 (d, J=5.05 Hz, 4H) 3.71-3.77 (m, 4H) 7.17 (s, 2H) 7.70-7.75 (m, 2H) 7.90 (d, J=8.72 Hz, 1H) 7.99-8.07 (m, 1H) 8.19 (d, J=8.21 Hz, 2H) 8.27 (br. s., 1H) 8.47 (s, 1H) 13.17 (d, J=8.97 Hz, 1H). MS (m/z) 528.0 M (+1), tR=1.41, Meth 10

Workup

  1. extractionThe crude was then extracted with EtOAc
  2. washthe combined extracts were washed with water, brine
  3. dry with materialdried with Na2SO4
  4. customThe volatiles were removed in vacuo
  5. customthe concentrate was purified on silica gel (ACN/DCM, 1:9 to 10:0)

Sources & evidence

ORD record
ord-649f908010a948bd8e0932689a33ea3c
Source dataset
uspto-grants-2011_02
Patent number
US07879850B2

Reaction notes

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