Triethyl orthoacetate → HCID 90023434, compound

HRID 56231Notes

Reaction equation

HRID 56231 reaction equation
[NH2:1]/[C:2](/[CH3:20])=[CH:3]\[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=[C:9]([Cl:19])[CH:8]=1)=[O:5].[C:21](OCC)(OCC)(OCC)[CH3:22]>>[Cl:19][C:9]1[CH:8]=[C:7]([N:6]2[C:4](=[O:5])[CH:3]=[C:2]([CH3:20])[N:1]=[C:21]2[CH3:22])[CH:12]=[CH:11][C:10]=1[N:13]1[CH2:14][CH2:15][O:16][CH2:17][CH2:18]1

Participants

3

Reactant 2

HCID 66221Triethyl orthoacetateHCID 90023336(Z)-3-amino-N-(3-chloro-4-morpholinophenyl)but-2-enamide

Product 1

HCID 90023434HCID 90023434, compoundYield 76%

Conditions

Temperature
150 °C

Procedure

A mixture of (Z)-3-amino-N-(3-chloro-4-morpholinophenyl)but-2-enamide (2.0 g, 6.76 mmol) and triethyl orthoacetate (20 mL) was stirred at 150° C. for 12 h. The mixture was cooled to rt and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=1:1) to give the title compound as a pale yellow solid (1.63 g, 76%). The compound was characterized by the following spectroscopic data:

Workup

  1. temperatureThe mixture was cooled to rt
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=1:1)

Sources & evidence

ORD record
ord-c411890db62842938db13daf7185fd9a
Source dataset
uspto-grants-2016_09
Patent number
US09434695B2

Reaction notes

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