Pyrazole → 1-(N-(2-isopropylvinyl)-N-tert.-butylcarbamyl)-pyrazole

HRID 1762857Notes

Reaction equation

[NH:1]1[CH:5]=[CH:4][CH:3]=[N:2]1.[CH:6]([CH:9]=[CH:10][N:11]([C:15]([CH3:18])([CH3:17])[CH3:16])[C:12](Cl)=[O:13])([CH3:8])[CH3:7].C(=O)([O-])[O-].[K+].[K+]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH:6]([CH:9]=[CH:10][N:11]([C:15]([CH3:17])([CH3:16])[CH3:18])[C:12]([N:1]1[CH:5]=[CH:4][CH:3]=[N:2]1)=[O:13])([CH3:8])[CH3:7]

Participants

Conditions

Temperature: 40 °C

Procedure

27.2 g (0.2 mole) of pyrazole, 1 g of 4-dimethylaminopyridine and 40.6 g (0.2 mole) of N-(2-isopropylvinyl)-N-tert.-butylcarbamyl chloride are added in succession to a suspension of 42 g of potassium carbonate in 150 ml of dry methylene chloride at 20° C. The mixture is stirred for 10 hours at 40° C., after which the resulting precipitate is filtered off under suction and washed with 200 ml of methylene chloride. The filtrate is washed with three times 80 ml of water, dried over Na2SO4 and evaporated down under reduced pressure, and the oil which remains is evaporated down under reduced pressure. 30.3 g of 1-(N-(2-isopropylvinyl)-N-tert.-butylcarbamyl)-pyrazole are obtained as a colorless liquid of boiling point 104°-105° C./0.3 mbar and nD 1.4828 (Compound No. 3).

Workup

filtrationafter which the resulting precipitate is filtered off under suction
washwashed with 200 ml of methylene chloride
washThe filtrate is washed with three times 80 ml of water
dry with materialdried over Na2SO4
customevaporated down under reduced pressure
customthe oil which remains is evaporated down under reduced pressure

Sources & evidence

ORD record: ord-bf9343b70db94b05abd91e64c1dd9577
Source dataset: uspto-grants-1989_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04835171

Reaction notes

Loading…