Toluene → HCID 178441959, compound

HRID 1645944Notes

Reaction equation

HRID 1645944 reaction equation
[CH2:1]([C:5]1[N:9]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH:18]([C:25]#[N:26])[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:13][CH:12]=2)[C:8]([S:27][CH2:28][C:29]2[CH:34]=[CH:33][C:32]([N+:35]([O-:37])=[O:36])=[CH:31][CH:30]=2)=[N:7][N:6]=1)[CH2:2][CH2:3][CH3:4].C[Sn]([N:42]=[N+:43]=[N-:44])(C)C.C1(C)C=CC=CC=1>C(Cl)Cl>[CH2:1]([C:5]1[N:9]([CH2:10][C:11]2[CH:12]=[CH:13][C:14]([O:17][CH:18]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:25]3[NH:44][N:43]=[N:42][N:26]=3)=[CH:15][CH:16]=2)[C:8]([S:27][CH2:28][C:29]2[CH:34]=[CH:33][C:32]([N+:35]([O-:37])=[O:36])=[CH:31][CH:30]=2)=[N:7][N:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 1140TolueneHCID 5104973Azido(trimethyl)stannaneHCID 19802761HCID 19802761, compound

Product 1

HCID 178441959HCID 178441959, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-butyl-4-[[4-[1-cyano-1-phenyl-methoxy]phenyl]methyl]-5-(4-nitrobenzylthio)-4H-1,2,4-triazole (from Example 3, Step B), trimethyltin azide (3.5 equivalents), and toluene is stirred at reflux for about 2 days. The mixture is then cooled and concentrated in vacuo. The residue is partitioned between 0.5N HCl and ethyl acetate. The ethyl acetate phase is dried (MgSO4), filtered, and concentrated. The residue is taken up in methanol and stirred with silica gel (4-5 g per mmol of cyano starting material) for about 1 hour. The mixture is then evaporated in vacuo to give a dry powder, which is layered on top of a column of silica gel packed in CH2Cl2. Elution of the column with a gradient of methanol in CH2Cl2 affords the title compound.

Workup

  1. temperatureat reflux for about 2 days
  2. temperatureThe mixture is then cooled
  3. concentrationconcentrated in vacuo
  4. customThe residue is partitioned between 0.5N HCl and ethyl acetate
  5. dry with materialThe ethyl acetate phase is dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. stirringstirred with silica gel (4-5 g per mmol of cyano starting material) for about 1 hour
  9. customThe mixture is then evaporated in vacuo
  10. customto give a dry powder, which
  11. washElution of the column with a gradient of methanol in CH2Cl2

Sources & evidence

ORD record
ord-e49e4c3f77fc430680714f5f2e52d302
Source dataset
uspto-grants-1993_01
Patent number
US05177095

Reaction notes

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