Diethyl Ether → HCID 11529633, compound

HRID 2185459Notes

Reaction equation

HRID 2185459 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=2)=[CH:3][CH:2]=1.C([O:17][CH:18]=[C:19]([C:25](OCC)=O)[C:20]([O:22][CH2:23][CH3:24])=[O:21])C.C(OCC)C>C1(OC2C=CC=CC=2)C=CC=CC=1>[CH2:7]([C:8]1[CH:13]=[C:12]2[C:11](=[CH:10][CH:9]=1)[NH:14][CH:25]=[C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:18]2=[O:17])[C:4]1[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 6871Diethyl (ethoxymethylene)malonateHCID 136914Benzenamine, 4-(phenylmethyl)-

Product 1

HCID 11529633HCID 11529633, compound

Reagents, catalysts & solvents 1

HCID 7583Diphenyl EtherSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 4-aminodiphenylmethane (20.3 g) and diethyl ethoxymethylenemalonate (24.3 mL) was heated at 110° C. for 3.5 hr under nitrogen. The resulting mixture was diluted with phenyl ether (50 mL) and heated at 220° C. for 7.5 hr. After cooling, ethyl ether was added to the reaction mixture. The precipitate was collected by filtration, and washed with ethyl ether to afford the title compound (12.6 g) as a pale brown powder: mp 265-270° C.; 1H NMR (400 MHz, CDCl3—CD3OD (1:1, v/v)) δ 1.39 (t, J=6.8 Hz, 3H), 4.12 (s, 2H), 4.35 (q, J=6.8 Hz, 2H), 7.14-7.33 (m, 4H), 7.47 (d, J=8.3 Hz, 1H), 7.55 (d, J=8.3 Hz, 1H), 7.65-7.75 (m, 2H), 8.23 (s, 1H), and 8.59 (s, 1H).

Workup

  1. temperatureheated at 220° C. for 7.5 hr
  2. temperatureAfter cooling
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with ethyl ether

Sources & evidence

ORD record
ord-c7c05ed37113444c9746de8c34d45e06
Source dataset
uspto-grants-2002_06
Patent number
US06399629B1

Reaction notes

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