Ethyl cyanoformate → HCID 135982325, compound

HRID 606504Notes

Reaction equation

HRID 606504 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][N:5]([CH2:11][CH2:12][O:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]([O:22][CH3:23])=[O:21])=[CH:16][CH:15]=2)[C:6]=1[C:7]([O:9]C)=O.[C:24]([C:26]([O:28][CH2:29][CH3:30])=[O:27])#[N:25].Cl.C(O)(=O)C>C(OCC)C>[CH3:23][O:22][C:20]([C:17]1[CH:18]=[CH:19][C:14]([O:13][CH2:12][CH2:11][N:5]2[C:6]3[C:7](=[O:9])[NH:25][C:24]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[N:1][C:2]=3[CH:3]=[N:4]2)=[CH:15][CH:16]=1)=[O:21]

Participants

5

Reactant 3

HCID 69336Ethyl cyanoformateHCID 22641269Acetate-hydrochloric acidHCID 59652119HCID 59652119, compound

Product 1

HCID 135982325HCID 135982325, compoundYield 67.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
90 °C

Procedure

Methyl 4-amino-1-[2-({4-[(methyloxy)carbonyl]phenyl}oxy)ethyl]-1H-pyrazole-5-carboxylate (2.18 g, 6.83 mmol) and ethyl cyanoformate (811 mg, 8.18 mmol) were added to 1N hydrogen chloride-acetic acid (40 mL), and the mixture was stirred under heating at 90° C. for 4 hr. After the mixture was allowed to cool, diethyl ether was added, and the precipitated crude crystals were collected by filtration, and washed with diethyl ether to give the title compound (1.79 g).

Workup

  1. temperatureto cool
  2. customthe precipitated crude crystals
  3. filtrationwere collected by filtration
  4. washwashed with diethyl ether

Sources & evidence

ORD record
ord-148bcfbcedd1421ab99461a9f950c880
Source dataset
uspto-grants-2011_03
Patent number
US07915267B2

Reaction notes

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