Benzene → HCID 54083964, compound

HRID 704646Notes

Reaction equation

HRID 704646 reaction equation
CO[CH:3]=[C:4]([CH3:8])[C:5](Cl)=[O:6].C1C=CC=CC=1.[OH:15][CH2:16][CH2:17][CH:18]1[CH2:20][CH:19]1[N:21]1C=CC(=O)[NH:24][C:22]1=[O:23].CN(C)C=O>[Ag]OC#N.C(OCC)C>[OH:15][CH2:16][CH2:17][CH:18]1[CH2:20][CH:19]1[N:21]1[CH:3]=[C:4]([CH3:8])[C:5](=[O:6])[NH:24][C:22]1=[O:23]

Participants

7

Reactant 4

HCID 241BenzeneHCID 6228DimethylformamideHCID 53919962HCID 53919962, compoundHCID 53969872HCID 53969872, compound

Product 1

HCID 54083964HCID 54083964, compound

Reagents, catalysts & solvents 2

HCID 178513473HCID 178513473, compoundCatalystHCID 3283Diethyl EtherSolvent

Conditions

Temperature
-15 °C

Procedure

3-Methoxymethacrylic acid chloride (2.68 g) and 25 mL of benzene are combined in a round bottom flask. To this mixture is added 6.4 g of silver cyanate and the resultant mixture heated to reflux temperature. After 40 min at reflux temperature the mixture is cooled to -15° C. In a separate round bottom flask, 1.0 g of the product of Step A of Example 8, 30 mL of dimethyl formamide (DMF) and 10 mL of diethyl ether are combined and this second mixture cooled to -15° C. The acylisocyanate mixture is added to the amine and the resultant solution stirred at -15° C. for 2 h. and allowed to stand in the refrigerator overnight. The reaction mixture is concentrated and the crude material is purified by column chromatography. The material recovered from the column and 5 mL of 2N aqueous sulfuric acid solution are combined in a round bottom flask and this reaction mixture heated at reflux temperature for 2 h. The mixture is adjusted to pH 7 with aqueous barium hydroxide, filtered and the filtrate concentrated. The residue is purified by column chromatography to afford the title compound.

Workup

  1. temperatureto reflux temperature
  2. temperatureAfter 40 min at reflux temperature the mixture
  3. temperaturethis second mixture cooled to -15° C
  4. customto stand in the refrigerator overnight
  5. concentrationThe reaction mixture is concentrated
  6. customthe crude material is purified by column chromatography
  7. customThe material recovered from the column and 5 mL of 2N aqueous sulfuric acid solution
  8. customare combined in a round bottom flask
  9. temperaturethis reaction mixture heated
  10. temperatureat reflux temperature for 2 h
  11. filtrationfiltered
  12. concentrationthe filtrate concentrated
  13. customThe residue is purified by column chromatography

Sources & evidence

ORD record
ord-b4a7fdb408494f4aba0540032848e457
Source dataset
uspto-grants-1991_01
Patent number
US04988703

Reaction notes

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