Cesium carbonate → HCID 67406788, compound

HRID 714656Notes

Reaction equation

HRID 714656 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH:14]3[CH2:16][CH2:15]3)[C:10](=[O:13])[NH:11][N:12]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[Br:23][C:24]1[CH:31]=[CH:30][CH:29]=[CH:28][C:25]=1[CH2:26]Br>C(#N)C>[Br:23][C:24]1[CH:31]=[CH:30][CH:29]=[CH:28][C:25]=1[CH2:26][N:11]1[C:10](=[O:13])[N:9]([CH:14]2[CH2:16][CH2:15]2)[C:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)=[N:12]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 769652-Bromobenzyl bromideHCID 580121993-(4-Chlorophenyl)-4-cyclopropyl-1H-1,2,4-triazol-5(4H)-one

Product 1

HCID 67406788HCID 67406788, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1.04 g (4.41 mmol) of 5-(4-chlorophenyl)-4-cyclopropyl-2,4-dihydro-3H-1,2,4-triazol-3-one [preparation according to WO 2007/134862 Example 36A] and 2.16 g (6.62 mmol) of cesium carbonate were suspended in 35 ml of acetonitrile, and 1.32 g (5.30 mmol) of 2-bromobenzyl bromide were added. The mixture was stirred under reflux for 18 h. The precipitated solid was then filtered off and the filtrate was concentrated under reduced pressure. The solid that remained was stirred in about 50 ml of diethyl ether and then filtered off and washed with a little diethyl ether. Drying under reduced pressure gave 1.05 g (59% of theory) of the target compound as a white solid.

Workup

  1. temperatureunder reflux for 18 h
  2. filtrationThe precipitated solid was then filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. stirringThe solid that remained was stirred in about 50 ml of diethyl ether
  5. filtrationfiltered off
  6. washwashed with a little diethyl ether
  7. customDrying under reduced pressure

Sources & evidence

ORD record
ord-bc8d6e66a5fc46d28bf3242e2ce16864
Source dataset
uspto-grants-2015_11
Patent number
US09187466B2

Reaction notes

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