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

HRID 353075Notes

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 l, 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-67f19ec7f553418b813f991a1a3f3459
Source dataset: uspto-grants-2004_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06750230B2

Reaction notes

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