Diisopropylethylamine → 2,2,2-Trichloroethyl 5-tert-butyl-3-(2-cyanopropan-2-yl)-2-methoxyphenylcarbamate

HRID 243812Notes

Reaction equation

HRID 243812 reaction equation
[NH2:1][C:2]1[C:3]([O:17][CH3:18])=[C:4]([C:12]([CH3:16])([CH3:15])[C:13]#[N:14])[CH:5]=[C:6]([C:8]([CH3:11])([CH3:10])[CH3:9])[CH:7]=1.Cl[C:20]([O:22][CH2:23][C:24]([Cl:27])([Cl:26])[Cl:25])=[O:21].C(N(CC)C(C)C)(C)C>C1COCC1>[C:8]([C:6]1[CH:5]=[C:4]([C:12]([C:13]#[N:14])([CH3:16])[CH3:15])[C:3]([O:17][CH3:18])=[C:2]([NH:1][C:20](=[O:21])[O:22][CH2:23][C:24]([Cl:27])([Cl:26])[Cl:25])[CH:7]=1)([CH3:11])([CH3:9])[CH3:10]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 870632,2,2-Trichloroethyl chloroformateHCID 681072452-(3-Amino-5-tert-butyl-2-methoxyphenyl)-2-methylpropanenitrile

Product 1

HCID 681074582,2,2-Trichloroethyl 5-tert-butyl-3-(2-cyanopropan-2-yl)-2-methoxyphenylcarbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(3-amino-5-tert-butyl-2-methoxyphenyl)-2-methylpropanenitrile (0.050 g, 0.202 mmol) in THF (0.6 mL), 2,2,2-trichloroethyl chloroformate (0.052 g, 0.245 mmol) and N,N-diisopropylethylamine (0.053 mL, 0.304 mmol) was added, and the mixture was stirred at room temperature for 2 hours. The reaction solution was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (ethyl acetate/n-hexane=0/100-30/70) to obtain 0.086 g (quantitative) of the captioned compound.

Workup

  1. customThe reaction solution was evaporated under reduced pressure
  2. customthe obtained residue was purified by silica gel column chromatography (ethyl acetate/n-hexane=0/100-30/70)
  3. customto obtain 0.086 g (quantitative) of the captioned compound

Sources & evidence

ORD record
ord-853e3abc9588446bbb24e15fbe4afc88
Source dataset
uspto-grants-2014_02
Patent number
US08653304B2

Reaction notes

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