Methyl N-(triethylammoniosulfonyl)carbamate → 2-(5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazol-3-yl)-5-propyl-1,3,4-oxadiazole

HRID 254806Notes

Reaction equation

HRID 254806 reaction equation
[C:1]([NH:6][NH:7][C:8]([C:10]1[C:14]([CH3:15])=[C:13]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)[N:12]([C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][C:24]=2[Cl:30])[N:11]=1)=O)(=[O:5])[CH2:2][CH2:3][CH3:4].CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC>C1COCC1>[Cl:22][C:19]1[CH:20]=[CH:21][C:16]([C:13]2[N:12]([C:23]3[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][C:24]=3[Cl:30])[N:11]=[C:10]([C:8]3[O:5][C:1]([CH2:2][CH2:3][CH3:4])=[N:6][N:7]=3)[C:14]=2[CH3:15])=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 2724994Methyl N-(triethylammoniosulfonyl)carbamateHCID 25149525N-butanoyl-N'-[5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carbonyl]-hydrazine

Product 1

HCID 251502372-(5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazol-3-yl)-5-propyl-1,3,4-oxadiazoleYield 61.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-butanoyl-N′-[5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carbonyl]-hydrazine (0.35 g, 0.75 mmol) obtained in Step 1 was added to a microwave reactor containing Burgess reagent (0.45 g, 1.88 mmol) in THF (2 mL). The capped reactor was placed in a microwave reactor and the mixture was irradiated at 140° C. for 15 min. The reaction product was purified by preparative HPLC to provide the title compound (0.21 g, 0.46 mmol, 61%) as yellow solid.

Workup

  1. customThe capped reactor was placed in a microwave reactor
  2. customthe mixture was irradiated at 140° C. for 15 min
  3. customThe reaction product was purified by preparative HPLC

Sources & evidence

ORD record
ord-07c7ae8b6e1e4300b41808ffa0f1c71b
Source dataset
uspto-grants-2011_01
Patent number
US07875647B2

Reaction notes

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