Diethyl (ethoxymethylene)malonate → HCID 178469640, compound

HRID 2290046Notes

Reaction equation

HRID 2290046 reaction equation
[CH2:1]([S:8][C:9]1[CH:10]=[C:11]([CH:13]=[CH:14][CH:15]=1)[NH2:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC[O:18][CH:19]=[C:20]([C:26](OCC)=O)[C:21]([O:23][CH2:24][CH3:25])=[O:22].CCCCCCC>C1(OC2C=CC=CC=2)C=CC=CC=1>[CH2:1]([S:8][C:9]1[CH:10]=[C:11]2[C:13]([C:19]([OH:18])=[C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH:26]=[N:12]2)=[CH:14][CH:15]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6871Diethyl (ethoxymethylene)malonateHCID 8900HeptaneHCID 118443953-(Benzylsulfanyl)aniline

Product 1

HCID 178469640HCID 178469640, compoundYield 71.3%

Reagents, catalysts & solvents 1

HCID 7583Diphenyl EtherSolvent

Conditions

Temperature
265 °C

Procedure

A mixture of 7.40 g of 3-(benzylsulfanyl)aniline from Preparation No. 28 and 7.70 g of diethyl ethoxymethylene malonate is heated at 135° C. under a gentle flow of argon for 2 h, then diluted with 30 mL of diphenyl ether and heated to 260-270° C. After 45 min, the solution was added to 500 mL of stirred heptane. The resulting solid was filtered, washed well with hexane, and dried under vacuum to afford 8.32 g of the title compound.

Workup

  1. customfrom Preparation No
  2. filtrationThe resulting solid was filtered
  3. washwashed well with hexane
  4. customdried under vacuum

Sources & evidence

ORD record
ord-eea9e6ed3deb44d6ab26eef78630ab5a
Source dataset
uspto-grants-2000_07
Patent number
US06093732

Reaction notes

Loading…