Diethyl (ethoxymethylene)malonate → HCID 178469810, compound

HRID 1470306Notes

Reaction equation

HRID 1470306 reaction equation
Cl.[N:2]1([C:7](=[NH:9])[NH2:8])[CH:6]=[CH:5][CH:4]=[N:3]1.OC1C(NC(=O)C(C2C=CC=CC=2)C2C=CC=CC=2)=CN=C(N2C=CC=N2)N=1.C[O-].[Na+].C([O:43][CH:44]=[C:45]([C:51](OCC)=O)[C:46]([O:48][CH2:49][CH3:50])=[O:47])C>CCO>[OH:43][C:44]1[C:45]([C:46]([O:48][CH2:49][CH3:50])=[O:47])=[CH:51][N:8]=[C:7]([N:2]2[CH:6]=[CH:5][CH:4]=[N:3]2)[N:9]=1

Participants

6

Reactant 4

HCID 6871Diethyl (ethoxymethylene)malonateHCID 2734672Pyrazole-1-carboxamidine monohydrochlorideHCID 10942334Sodium MethoxideHCID 178522405HCID 178522405, compound2×

Product 1

HCID 178469810HCID 178469810, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

1H-pyrazole-1-carboximidamide hydrochloride, compound 2-a from Example 2, (22.11 g, 0.15 mol) in EtOH (250 ml) was added sodium methoxide (12.3 g, 0.23 mol) and diethyl ethoxymethylenemalonate, compound 2-b from Example 2, (30 ml, 0.15 mol). The reaction was heated for about 40 min at 75° C. and then cooled to room temperature. The mixture was filtered and the solid was washed with ethanol and ether and dried under vacuum to give compound 3-a (21 g, 60%). 1H NMR (DMSO-d6, 300 MHz): δ 8.50 (m, 2H), 7.70 (s, 1H), 6.47 (m, 1H), 4.13 (m, 2H), 1.24 (m, 3H).

Workup

  1. temperaturecooled to room temperature
  2. filtrationThe mixture was filtered
  3. washthe solid was washed with ethanol and ether
  4. customdried under vacuum

Sources & evidence

ORD record
ord-ae27aac3723c4a548b35317638a111d7
Source dataset
uspto-grants-2015_04
Patent number
US09006433B2

Reaction notes

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