Fipronil → HCID 86605668, compound

HRID 2109481Notes

Reaction equation

HRID 2109481 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:17])([F:16])[F:15])=[CH:9][C:8]=2[Cl:18])[N:5]=[C:4]([C:19]#[N:20])[C:3]=1[S:21]([C:23]([F:26])([F:25])[F:24])=O.[CH2:27]([O:34][C:35]([NH:37][CH2:38][CH2:39][C:40](O)=[O:41])=[O:36])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C1(N=C=NC2CCCCC2)CCCCC1.C(OCC)(=O)C>O1CCOCC1.CN(C)C1C=CN=CC=1.CCCCCCC.C(OCC)(=O)C.O>[Cl:18][C:8]1[CH:9]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:11]=[C:12]([Cl:13])[C:7]=1[N:6]1[C:2]([NH:1][C:40](=[O:41])[CH2:39][CH2:38][NH:37][C:35]([O:34][CH2:27][C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)=[O:36])=[C:3]([S:21][C:23]([F:26])([F:25])[F:24])[C:4]([C:19]#[N:20])=[N:5]1

Participants

9

Reactant 4

HCID 3352FipronilHCID 8857Ethyl AcetateHCID 10868DicyclohexylcarbodiimideHCID 75313N-Benzyloxycarbonyl-beta-alanine

Product 1

HCID 86605668HCID 86605668, compound

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolventHCID 21899848Ethylacetate heptaneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-4-trifluoromethylsulfinylpyrazole (1.0 g, 2.29 mmol) in dioxan, benzyloxycarbonyl-beta-alanine (0.56 g, 2.5 mmol), dicyclohexylcarbodiimide (0.61 g, 2.9 mmol) and 4-dimethylaminopyridine (0.06 g, 0.46 mmol) were added. The mixture was stirred at 25° C. for 24 hours. After extractive workup (ethyl acetate, water) and column chromatography with heptane-ethyl acetate (1:1) the title product was obtained (0.81 g).

Sources & evidence

ORD record
ord-6a3b3e836fe7493490557a2664b627c3
Source dataset
uspto-grants-2009_04
Patent number
US07514561B2

Reaction notes

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