Ethyl chloroacetate → Ethyl 2-[3-(3-chloro-4-methyl-2-thienyl)-4-isobutyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-acetate

HRID 660914Notes

Reaction equation

HRID 660914 reaction equation
C(=O)([O-])[O-].[K+].[K+].[Cl:7][C:8]1[C:12]([CH3:13])=[CH:11][S:10][C:9]=1[C:14]1[N:15]([CH2:20][CH:21]([CH3:23])[CH3:22])[C:16](=[O:19])[NH:17][N:18]=1.Cl[CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27]>C(#N)C>[Cl:7][C:8]1[C:12]([CH3:13])=[CH:11][S:10][C:9]=1[C:14]1[N:15]([CH2:20][CH:21]([CH3:23])[CH3:22])[C:16](=[O:19])[N:17]([CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])[N:18]=1

Participants

5

Reactant 3

HCID 7751Ethyl chloroacetateHCID 11430Potassium CarbonateHCID 580116455-(3-chloro-4-methyl-2-thienyl)-4-isobutyl-2,4-dihydro-3H-1,2,4-triazol-3-one

Product 1

HCID 58011923Ethyl 2-[3-(3-chloro-4-methyl-2-thienyl)-4-isobutyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-acetate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

570 mg (4.12 mmol) of potassium carbonate are added to a suspension of 560 mg (2.06 mmol) of 5-(3-chloro-4-methyl-2-thienyl)-4-isobutyl-2,4-dihydro-3H-1,2,4-triazol-3-one from Example 247A and 253 mg (2.06 mmol) of ethyl chloroacetate in 10 ml acetonitrile and heated for 4 hrs under reflux. For the workup, this is concentrated, and the residue taken up in water and extracted three times with ethyl acetate. The combined organic phases are concentrated, and the crude product remaining as the residue is purified by preparative HPLC [Method 12]. 705 mg (96% of theory) of the target compound are thus obtained.

Workup

  1. temperatureheated for 4 hrs
  2. temperatureunder reflux
  3. concentrationFor the workup, this is concentrated
  4. extractionextracted three times with ethyl acetate
  5. concentrationThe combined organic phases are concentrated
  6. customis purified by preparative HPLC [Method 12]
  7. custom705 mg (96% of theory) of the target compound are thus obtained

Sources & evidence

ORD record
ord-80f3279430664672af91d1fc59e39358
Source dataset
uspto-grants-2011_12
Patent number
US08084481B2

Reaction notes

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