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Cesium carbonate → Ethyl rac-2-[3-(4-chlorophenyl)-4-cyclopropyl-5-oxo-4,5-dihydro-1h-1,2,4-triazol-1-yl]propionate

HRID 660857
Notes
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Reaction equation

HRID 660857 reaction equation
Br[CH:2]([CH3:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4].C(=O)([O-])[O-].[Cs+].[Cs+].[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[N:23]([CH:28]3[CH2:30][CH2:29]3)[C:24](=[O:27])[NH:25][N:26]=2)=[CH:18][CH:17]=1>C(#N)C>[Cl:15][C:16]1[CH:17]=[CH:18][C:19]([C:22]2[N:23]([CH:28]3[CH2:29][CH2:30]3)[C:24](=[O:27])[N:25]([CH:2]([CH3:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4])[N:26]=2)=[CH:20][CH:21]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 79040Ethyl 2-bromopropionateHCID 580121993-(4-Chlorophenyl)-4-cyclopropyl-1H-1,2,4-triazol-5(4H)-one

Product 1

HCID 58012037Ethyl rac-2-[3-(4-chlorophenyl)-4-cyclopropyl-5-oxo-4,5-dihydro-1h-1,2,4-triazol-1-yl]propionate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
85 °C

Procedure

384 mg (2.12 mmol) of ethyl 2-bromopropionate and 1.38 g (4.24 mmol) of caesium carbonate are added to 500 mg (2.12 mmol) of 5-(4-chlorophenyl)-4-cyclopropyl-2,4-dihydro-3H-1,2,4-triazol-3-one from Example 36A in 5 ml acetonitrile and the reaction mixture is heated at 85° C. overnight. It is then concentrated in vacuo, the residue is partitioned between water and dichloromethane, and the separated organic phase is dried over sodium sulphate and again evaporated. After purification of the residue by flash chromatography over silica gel (eluent: first dichloromethane, then dichloromethane/methanol 200:1), 729 mg (97% of theory) of the target compound are obtained.

Workup

  1. concentrationIt is then concentrated in vacuo
  2. customthe residue is partitioned between water and dichloromethane
  3. dry with materialthe separated organic phase is dried over sodium sulphate
  4. customagain evaporated
  5. customAfter purification of the residue by flash chromatography over silica gel (eluent
  6. customfirst dichloromethane, then dichloromethane/methanol 200:1), 729 mg (97% of theory) of the target compound are obtained

Sources & evidence

ORD record
ord-33b5651bcaa24a30bbe7abb571a57d20
Source dataset
uspto-grants-2011_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08084481B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes