Triethylamine → HCID 178463175, compound

71.5 g of chlorine is passed into a solution of 75.5 g of 1-ethyl-3-hydroxy-1,2,4-triazole and 185 ml of triethylamine in 800 ml of absolute ethanol. The exothermic reaction is kept at 20° to 30°C while cooling. Triethylamine hydrochloride is precipitated. The batch is further stirred for 2 hours after the chlorine has been passed in. Triethylamine hydrochloride is filtered off and the filtrate concentrated. The residue is dissolved in 500 ml of ether and 500 ml of water. The phases are separated and the aqueous phase is extracted 3 times with 300 ml of ether each time. The ethereal extracts are dried over sodium sulphate. The drying agent is filtered off and the filtrate concentrated. The residue is recrystallised from a mixture of 400 ml of xylene and 250 ml of ligroin and dried in vacuo. Yield: 28.7 g (29 % of theory); m.p. 108°-110°C.

1. customThe exothermic reaction
2. customis kept at 20° to 30°C
3. temperaturewhile cooling
4. customTriethylamine hydrochloride is precipitated
5. filtrationTriethylamine hydrochloride is filtered off
6. concentrationthe filtrate concentrated
7. dissolutionThe residue is dissolved in 500 ml of ether
8. customThe phases are separated
9. extractionthe aqueous phase is extracted 3 times with 300 ml of ether each time
10. dry with materialThe ethereal extracts are dried over sodium sulphate
11. filtrationThe drying agent is filtered off
12. concentrationthe filtrate concentrated
13. customThe residue is recrystallised from a mixture of 400 ml of xylene and 250 ml of ligroin
14. customdried in vacuo

ORD record

ord-e9fd02d4bf4f46fba2bef278646040c8

Source dataset

uspto-grants-1976_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US03932629