Triethylamine → HCID 19802761, compound

HRID 1645943Notes

Reaction equation

HRID 1645943 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](=O)[NH2:26])[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:13][CH:12]=2)[C:8]([S:28][CH2:29][C:30]2[CH:35]=[CH:34][C:33]([N+:36]([O-:38])=[O:37])=[CH:32][CH:31]=2)=[N:7][N:6]=1)[CH2:2][CH2:3][CH3:4].P(Cl)(Cl)(Cl)=O.C(N(CC)CC)C>>[CH2:1]([C:5]1[N:9]([CH2:10][C:11]2[CH:12]=[CH:13][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:15][CH:16]=2)[C:8]([S:28][CH2:29][C:30]2[CH:35]=[CH:34][C:33]([N+:36]([O-:38])=[O:37])=[CH:32][CH:31]=2)=[N:7][N:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 19802748HCID 19802748, compound

Product 1

HCID 19802761HCID 19802761, compound

Procedure

A suspension of 3-butyl-4-[[4-[1-carbamoyl-1-phenylmethoxy]phenyl]methyl]-5-(4-nitrobenzylthio)-4H-1,2,4-triazole (from Example 3, Step A) in phosphorus oxychloride (25-30 equivalents) is stirred at 0° C. under N2 as triethylamine (2.2 equivalents) is added dropwise over about 1 hours. After the addition is complete, the mixture is gradually warmed to room temperature and then heated to reflux for about 45 minutes or until TLC indicates complete reaction. The cooled mixture is concentrated in vacuo, and the residue is partitioned between ice-water and an organic solvent, such as ether, ethyl acetate, or toluene. The organic phase is washed with dilute NaOH and then with H2O. The organic solution is dried over MgSO4, filtered, and concentrated to give the title compound, which is used directly or may be purified by chromatography on silica gel.

Workup

  1. additionis added dropwise over about 1 hours
  2. additionAfter the addition
  3. temperatureheated
  4. temperatureto reflux for about 45 minutes or until TLC
  5. customreaction
  6. concentrationThe cooled mixture is concentrated in vacuo
  7. customthe residue is partitioned between ice-water
  8. washThe organic phase is washed with dilute NaOH
  9. dry with materialThe organic solution is dried over MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-8f5a90ea397e4774b994597f0f89d28b
Source dataset
uspto-grants-1993_01
Patent number
US05177095

Reaction notes

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