Trichloroacetyl isocyanate → [4-(3,5-Dichlorobenzyl)-3,5-diethyl-1h-pyrazol-1-yl]methyl carbamate

HRID 723599Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:17]=[C:18]([Cl:20])[CH:19]=1)[CH2:5][C:6]1[C:7]([CH2:15][CH3:16])=[N:8][N:9]([CH2:13][OH:14])[C:10]=1[CH2:11][CH3:12].ClC(Cl)(Cl)[C:23]([N:25]=C=O)=[O:24]>ClCCl>[C:23](=[O:24])([O:14][CH2:13][N:9]1[C:10]([CH2:11][CH3:12])=[C:6]([CH2:5][C:4]2[CH:17]=[C:18]([Cl:20])[CH:19]=[C:2]([Cl:1])[CH:3]=2)[C:7]([CH2:15][CH3:16])=[N:8]1)[NH2:25]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of the alcohol of Example 41 (280 mg, 0.90 mmol) in dichloromethane (5 ml) was cooled to 0° C., treated with trichloroacetyl isocyanate (128 μl, 1.1 mmol) and stirred at 0° C. for 30 minutes. The solution was soaked into a pad of alumina (neutral, activity II, Brockmann), washed with dichloromethane and then extracted with ethyl acetate. The organic extract was concentrated under reduced pressure. The crude material was purified by flash chromatography on silica gel eluting with a solvent gradient of cyclohexane:ethyl acetate (2:1, by volume) gradually changing to cyclohexane:ethyl acetate (1:1, by volume) to afford the title compound (238 mg) as a solid, m.p. 153–155° C.

Workup

washwashed with dichloromethane
extractionextracted with ethyl acetate
extractionThe organic extract
concentrationwas concentrated under reduced pressure
customThe crude material was purified by flash chromatography on silica gel eluting with a solvent gradient of cyclohexane:ethyl acetate (2:1, by volume)

Sources & evidence

ORD record: ord-2647dd066c094c13a3adcb2d7eaf697d
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07141585B2

Reaction notes

Loading…