Ethyl orthoformate → HCID 53708904, compound

HRID 989240Notes

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]([CH3:23])=[O:22].[CH:24](OCC)(OCC)[O:25][CH2:26][CH3:27]>>[Cl:18][C:8]1[CH:9]=[C:10]([C:14]([F:15])([F:16])[F:17])[CH:11]=[C:12]([Cl:13])[C:7]=1[N:6]1[C:2]([N:1]=[CH:24][O:25][CH2:26][CH3:27])=[C:3]([S:21]([CH3:23])=[O:22])[C:4]([C:19]#[N:20])=[N:5]1

Participants

Reactant 2

HCID 31214Ethyl orthoformate

HCID 10861895HCID 10861895, compound

Product 1

HCID 53708904HCID 53708904, compound

Conditions

Temperature: 20 °C

Procedure

A solution of 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfinyl-1H-pyrazole-3-carbonitrile (4.92 g) in triethyl orthoformate (100 ml) was heated under reflux for two hours, then stirred at 20° C. for 16 hours and evaporated. Trituration with boiling hexane gave 1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-5-[(ethoxymethylene)amino]-4-methylsulfinyl-1H-pyrazole-3-carbonitrile (4.05 g), m.p.93-95° C. By proceeding in a similar manner the following compound was prepared:

Workup

temperatureunder reflux for two hours
customevaporated

Sources & evidence

ORD record: ord-e02877030b9648c8af9b60b795191feb
Source dataset: uspto-grants-2003_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06638956B2

Reaction notes

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