Potassium Carbonate → HCID 19802732, compound

HRID 1645940Notes

Reaction equation

HRID 1645940 reaction equation
[CH2:1]([C:5]1[N:9]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)[C:8]([S:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=2)=[N:7][N:6]=1)[CH2:2][CH2:3][CH3:4].Br[CH:30]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:31]([O:33][CH3:34])=[O:32].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH2:1]([C:5]1[N:9]([CH2:10][C:11]2[CH:12]=[CH:13][C:14]([O:17][CH:30]([C:31]([O:33][CH3:34])=[O:32])[C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[CH:15][CH:16]=2)[C:8]([S:18][CH2:19][C:20]2[CH:21]=[CH:22][C:23]([N+:26]([O-:28])=[O:27])=[CH:24][CH:25]=2)=[N:7][N:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 137806Benzeneacetic acid, alpha-bromo-, methyl esterHCID 19802745HCID 19802745, compound

Product 1

HCID 19802732HCID 19802732, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 322 mg (0.81 mmol) of 3-butyl-4-(4-hydroxybenzyl)-5-(4-nitrobenzylthio) -(4H-1,2,4-triazole (Example 1, Step E), 278 mg (1.21 mmol) of methyl α-bromophenylacetate, 168 mg (1.22 mmol) of anhydrous K2CO3, and 3 ml of dry DMF was stirred under N2 at 60° C. for 24 hours. The mixture was concentrated in vacuo (oil pump, 50° C.), and the residue was partitioned between EtOAc and H2O. The organic solution was dried (MgSO4), filtered, and concentrated. The residual oil was chromatographed on a column of silica gel (elution with a gradient of 0.5-10% MeOH in CH2Cl2). TLC (97:3 CHCl3 -iPrOH and 98:2 CH2Cl2 -MeOH) and NMR were used to identify the appropriate product fractions, which were combined and concentrated to give the product as a gum.

Workup

  1. concentrationThe mixture was concentrated in vacuo (oil pump, 50° C.)
  2. customthe residue was partitioned between EtOAc and H2O
  3. dry with materialThe organic solution was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residual oil was chromatographed on a column of silica gel (
  7. washelution with a gradient of 0.5-10% MeOH in CH2Cl2)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-aa08eb57cd1a41718be9ce9bac7181c3
Source dataset
uspto-grants-1993_01
Patent number
US05177095

Reaction notes

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