Hydrochloric Acid → HCID 16225331, compound

HRID 390601Notes

Reaction equation

HRID 390601 reaction equation
[ClH:1].[CH2:2]([O:4]/[C:5](=[CH:9]\[C:10]1[CH:11]=[N:12][C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([N:22]([CH3:33])[C:23]([NH:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[O:24])[CH:17]=2)=[CH:14][CH:15]=1)/[C:6]([OH:8])=[O:7])[CH3:3]>C(O)C>[ClH:1].[CH2:2]([O:4]/[C:5](=[CH:9]\[C:10]1[CH:11]=[N:12][C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([N:22]([CH3:33])[C:23]([NH:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[O:24])[CH:17]=2)=[CH:14][CH:15]=1)/[C:6]([OH:8])=[O:7])[CH3:3]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 16225332HCID 16225332, compound

Product 1

HCID 16225331HCID 16225331, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.3 mL (0.3 mmol) of a 1 N ethanolic hydrogen chloride solution is added to a solution of 0.12 g (0.3 mmol) of (Z)-2-ethoxy-3-{6-[3-(3-heptyl-1-methylureido)phenyl]pyrid-3-yl}acrylic acid in 1 mL of ethanol, precooled to 0° C. The ethanol is evaporated off under a flow of nitrogen and 6 mL of diethyl ether are added. The hydrochloride precipitates; the reaction medium is filtered off and the solid obtained is rinsed thoroughly with diethyl ether. The solid obtained is recrystallized from a hot mixture of acetone and a minimum amount of water. 100 mg (77%) of (Z)-2-ethoxy-3-{6-[3-(3-heptyl-1-methylureido)phenyl]pyrid-3-yl}acrylic acid hydrochloride are obtained in the form of a yellow solid with a melting point of 170° C.

Workup

  1. customprecooled to 0° C
  2. customThe ethanol is evaporated off under a flow of nitrogen and 6 mL of diethyl ether
  3. additionare added
  4. customThe hydrochloride precipitates
  5. filtrationthe reaction medium is filtered off
  6. customthe solid obtained
  7. washis rinsed thoroughly with diethyl ether
  8. customThe solid obtained
  9. customis recrystallized from a hot mixture of acetone

Sources & evidence

ORD record
ord-3b9e7c763bc942baa50923268845f4f8
Source dataset
uspto-grants-2013_02
Patent number
US08383652B2

Reaction notes

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