Diethyl Malonate → HCID 178516639, compound

HRID 895459Notes

Reaction equation

HRID 895459 reaction equation
Cl.[C:2]([NH2:10])(=[NH:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:11](OCC)(=[O:18])[CH2:12][C:13](OCC)=[O:14].C1CCN2C(=NCCC2)CC1>CN(C=O)C>[C:3]1([C:2]2[N:10]=[C:13]([OH:14])[CH:12]=[C:11]([OH:18])[N:9]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 7761Diethyl MalonateHCID 80289Benzamidine, hydrochlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

Product 1

HCID 178516639HCID 178516639, compoundYield 73.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of benzamidine hydrochloride (44.41 g; 0.284 mol), diethyl malonate (45.51 g; 0.284 mol) and DBU (86.40 g; 0.568 mol) in DMF (250 mL) was heated at 85° C. for 20 h. After cooling to room temperature, the flask was placed in a refrigerator overnight. The crystalline product was collected by filtration and washed with DMF (300 mL), then dissolved in water (ca. 110 mL) and acidified with 2 M HCl (110 mL) with water added, as necessary, to maintain a suspension. The product was collected by filtration, washed with water (100 mL) and dried to a constant weight under high vacuum giving 39.09 g (73%) of an off-white solid. LC (method B) tR=6.2 min; 1H NMR (200 MHz, DMSO-d6) δ 8.08 (m, 2H), 7.54 (m, 3H), 5.34 (s, 1H); ESIMS 189.0 ([M+H]+).

Workup

  1. customwas placed in a refrigerator overnight
  2. filtrationThe crystalline product was collected by filtration
  3. washwashed with DMF (300 mL)
  4. dissolutiondissolved in water (ca. 110 mL)
  5. additionadded
  6. temperatureas necessary, to maintain a suspension
  7. filtrationThe product was collected by filtration
  8. washwashed with water (100 mL)
  9. customdried to a constant weight under high vacuum

Sources & evidence

ORD record
ord-9597b43b20ee4c6899b78e514616b60d
Source dataset
uspto-grants-2005_07
Patent number
US06916804B2

Reaction notes

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