3-Ethoxy-2-methyl-2-propenal → HCID 12056717, compound

HRID 1060522Notes

Reaction equation

HRID 1060522 reaction equation
O.O.Cl.[F:4][C:5]([F:16])([F:15])[C:6]1[CH:14]=[CH:13][C:9]([C:10]([NH2:12])=[NH:11])=[CH:8][CH:7]=1.C(O[CH:20]=[C:21]([CH3:24])[CH:22]=O)C.C[O-].[Na+]>CO>[CH3:24][C:21]1[CH:20]=[N:11][C:10]([C:9]2[CH:13]=[CH:14][C:6]([C:5]([F:15])([F:16])[F:4])=[CH:7][CH:8]=2)=[N:12][CH:22]=1

Participants

5

Reactant 3

HCID 5591983-Ethoxy-2-methyl-2-propenalHCID 10942334Sodium MethoxideHCID 446307714-(Trifluoromethyl)benzene-1-carboximidamide--hydrogen chloride--water (1/1/2)

Product 1

HCID 12056717HCID 12056717, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A sample of 4-trifluoromethylbenzamidine hydrochloride dihydrate (Maybridge, 15.2 g, 58 mmol) was dissolved in 100 mL of methanol and 3-ethoxy-2-methylacrolein (Janssen, 7.8 g, 64 mmol) was added. Sodium methoxide (25% solution in methanol, 14.7 mL) was added and the mixture was heated at 50° C. for 3 h. The cooled reaction mixture was then dded to 500 ml of ice water and stirred for 30 minutes. The white solid was filtered, air dried, dissolved in 300 mL of dichloromethane and dried over magnesium sulfate. The solvent was removed under reduced pressure to yield, after trituration with hexanes, 12.5 g of the product as a white solid melting at 143-146° C. 1H NMR (CDCl3): δ2.37 (s, 3H), 7.73 (d, 2H), 8.53 (d, 2H), 8.66 (s, 2H).

Workup

  1. customThe cooled reaction mixture
  2. filtrationThe white solid was filtered
  3. customair dried
  4. dissolutiondissolved in 300 mL of dichloromethane
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was removed under reduced pressure
  7. customto yield

Sources & evidence

ORD record
ord-8107a03512de4b559c7e3dba5f308ee3
Source dataset
uspto-grants-2003_02
Patent number
US06525001B1

Reaction notes

Loading…