Boron trifluoride etherate → HCID 20025903, compound

HRID 1722982Notes

Reaction equation

[B:1]([F:4])([F:3])[F:2].CCOCC.[NH2:10][C:11]1[C:12]([Cl:31])=[CH:13][C:14]([F:30])=[C:15]([N:17]2[C:22](=[O:23])[CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[N:19]([CH3:28])[C:18]2=[O:29])[CH:16]=1.[N:32](OCCC(C)C)=O.CCCCC>C(Cl)Cl>[F:2][B-:1]([F:25])([F:4])[F:3].[Cl:31][C:12]1[CH:13]=[C:14]([F:30])[C:15]([N:17]2[C:22](=[O:23])[CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[N:19]([CH3:28])[C:18]2=[O:29])=[CH:16][C:11]=1[N+:10]#[N:32]

Participants

Conditions

Temperature: 5 °C

Procedure

4.24 g of boron trifluoride etherate and 6.75 g of 3-(5-amino-4-chloro-2-fluorophenyl)-1 -methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione are placed at -15° C. in 50 ml of methylene chloride. A solution of 3.2 ml of isopentyl nitrite in 20 ml of methylene chloride is added dropwise to the mixture within 20 minutes while cooling. The mixture is subsequently stirred at 5° C. for 45 minutes, 25 treated with 50 ml of n-pentane and the resulting crystals are filtered off. There is obtained 2-chloro-5-[3,6-dihydro-2,6-dioxo -3-methyl-4-trifluoromethyl-1(2H)-pyrimidinyl]-4-fluorobenzenediazonium tetrafluoroborate. m.p. 191° C. (decomposition).

Workup

temperaturewhile cooling
filtrationthe resulting crystals are filtered off

Sources & evidence

ORD record: ord-3ba3c9cbdb0943af9772f7f34b711553
Source dataset: uspto-grants-1989_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04859229

Reaction notes

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