Tetrahydrofuran → HCID 20316381, compound

HRID 436704Notes

Reaction equation

HRID 436704 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][C:17]=1[Cl:18])[CH2:5][NH:6][C:7](=[O:14])[C:8]([C:12]#[N:13])=[C:9]([CH3:11])[CH3:10].[CH3:19]OC(OC)N(C)C.O1CCCC1>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][C:17]=1[Cl:18])[CH2:5][N:6]1[CH:19]=[CH:10][C:9]([CH3:11])=[C:8]([C:12]#[N:13])[C:7]1=[O:14]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 78373Dimethylformamide dimethyl acetalHCID 20316355HCID 20316355, compound

Product 1

HCID 20316381HCID 20316381, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 42.8 g. (0.15 mole) of N-(3,4-dichlorobenzyl)-2-cyano-3-methylcrotonamide and 18.0 g. (0.15 mole) of N,N-dimethylformamide dimethyl acetal in 250 ml. of tetrahydrofuran is stirred at ambient temperature for 22 hr. followed by 1 hr. at reflux. The solvent is removed and the tacky solid residue is heated until molten. When evolution of dimethylamine subsides the reaction mixture is allowed to cool and the dark glassy residue is recrystallized from ethanol. The solid product is slurried in ether and isolated by filtration to give 15.79 g. (36%) of product as a brown powder: m.p. 177.5°-180.5° C.; ν (ethanol) 2210 (CN) and 1670 cm.-1 (C=O); δ 8.19 (d, 1H, H6), 7.2-7.8 (m, 3H, aromatic protons), 6.46 (d, 1H, H5), 5.16 (s, 2H, benzyl methylene), and 2.4 (s, 3H, methyl).

Workup

  1. temperatureat reflux
  2. customThe solvent is removed
  3. temperaturethe tacky solid residue is heated
  4. temperatureto cool
  5. customthe dark glassy residue is recrystallized from ethanol
  6. customisolated by filtration
  7. customto give 15.79 g

Sources & evidence

ORD record
ord-d4b822c3b10c4bd9a4ba9c13661905ce
Source dataset
uspto-grants-1977_06
Patent number
US04028084

Reaction notes

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