Hydrochloric Acid → HCID 131730027, compound

HRID 2065955Notes

Reaction equation

HRID 2065955 reaction equation
[O:1]=[C:2]([CH3:8])/[CH:3]=[CH:4]/[C:5]([OH:7])=O.[CH2:9](N)[CH3:10].CC[N:14]=C=NCCCN(C)C.Cl.Cl>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH2:9](/[C:4](=[CH:3]\[C:2](=[O:1])[CH3:8])/[C:5]([NH2:14])=[O:7])[CH3:10]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6341EthylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 5363652(2E)-4-Oxo-2-pentenoic acid

Product 1

HCID 131730027HCID 131730027, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

(2E)-4-Oxopent-2-enoic acid (9.41 g, 80 mmol) and EtNH2 (2 M in THF, 40 ml, 80 mmol) are dissolved in CH2Cl2 (250 ml). The solution is cooled to 0° C. Then DMAP (1.47 g, 12 mmol) and EDCl (15.34 g, 80 mmol) are added. The resulting suspension is stirred for 17 h at 0 (C. Then the reaction mixture is poured into 2 M HCl (100 ml) and extracted with CH2Cl2 (2×1 l). The organic phases are washed with 2 M HCl (50 ml), saturated NaHCO3 (50 ml) and brine (100 ml) successively. The combined organic phases are dried with Na2SO4 and evaporated under reduced pressure at 40° C. 24 (ethyl (2E)-4-oxopent-2-enamide) (5.74 g, 51%) is obtained as a brown solid.

Workup

  1. extractionextracted with CH2Cl2 (2×1 l)
  2. washThe organic phases are washed with 2 M HCl (50 ml), saturated NaHCO3 (50 ml) and brine (100 ml) successively
  3. dry with materialThe combined organic phases are dried with Na2SO4
  4. customevaporated under reduced pressure at 40° C

Sources & evidence

ORD record
ord-d1490771ae734707adc9b875c3587121
Source dataset
uspto-grants-2012_10
Patent number
US08288566B2

Reaction notes

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