N-(5,7-dichloro-2,3-dihydrobenzofuran-2-ylmethyl)-N-butylcarbamyl chloride → 1-(N-(5,7-dichloro-2,3-dihydrobenzofuran-2-ylmethyl)-N-butylcarbamyl)-1,2,4-triazole

HRID 1248931Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([Cl:20])[C:5]2[O:9][CH:8]([CH2:10][N:11]([CH2:15][CH2:16][CH2:17][CH3:18])[C:12](Cl)=[O:13])[CH2:7][C:6]=2[CH:19]=1.[NH:21]1[CH:25]=[N:24][C-:23]=[N:22]1.[Na+]>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([Cl:20])[C:5]2[O:9][CH:8]([CH2:10][N:11]([CH2:15][CH2:16][CH2:17][CH3:18])[C:12]([N:21]3[CH:25]=[N:24][CH:23]=[N:22]3)=[O:13])[CH2:7][C:6]=2[CH:19]=1

Participants

Conditions

Temperature: 65 °C

Procedure

13.5 g (0.04 mole) of N-(5,7-dichloro-2,3-dihydrobenzofuran-2-ylmethyl)-N-butylcarbamyl chloride were added dropwise to a suspension of 5.5 g (0.06 mole) of sodium 1,2,4-triazolide in 120 ml of dry tetrahydrofuran at 20° C. The mixture was stirred for 6 hours at 65° C., after which it was cooled to 20° C., and the precipitate was filtered off under suction. The filtrate was evaporated down, the residue was suspended in 30 ml of diethyl ether, and the product was filtered off under suction. 13.1 g of 1-(N-(5,7-dichloro-2,3-dihydrobenzofuran-2-ylmethyl)-N-butylcarbamyl)-1,2,4-triazole were obtained as colorless crystals of melting point 122°-124° C. (compound NO. 2).

Workup

temperatureafter which it was cooled to 20° C.
filtrationthe precipitate was filtered off under suction
customThe filtrate was evaporated down
filtrationthe product was filtered off under suction

Sources & evidence

ORD record: ord-93532d0c347b4f2fa44558b967e4ab14
Source dataset: uspto-grants-1986_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04628058

Reaction notes

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