Hydrochloric Acid → 69193-39-1

HRID 602352Notes

Reaction equation

HRID 602352 reaction equation
[Cl:1][C:2]1[S:6][C:5]([CH:7]=O)=[CH:4][CH:3]=1.C(O)(=O)[CH2:10][C:11]([OH:13])=[O:12].O.Cl>N1CCCCC1.N1C=CC=CC=1>[Cl:1][C:2]1[S:6][C:5](/[CH:7]=[CH:10]/[C:11]([OH:13])=[O:12])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 867Malonic AcidHCID 962WaterHCID 817002-Thiophenecarboxaldehyde, 5-chloro-

Product 1

HCID 1310045069193-39-1Yield 81.7%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8082PiperidineSolvent

Procedure

The solution of 1 g (6.62 mmol) of 5-chloro-2-thiophenecarboxaldehyde and 1.38 g (13.23 mmol) of malonic acid in 0.07 ml of piperidine and 5 ml of pyridine is refluxed for 2 hours. The reaction solution is subsequently allowed to cool, then poured into 20 ml of water and acidified to pH 1 using 2N hydrochloric acid. The product which precipitates in the process is filtered off with suction and dried in a drying cabinet at 80° C., giving 1.02 g of (E)-3-(5-chlorothiophen-2-yl)acrylic acid as brown crystals, ESI 189. Analogously to Example 7.1, reaction between the compound of Example 7.2 and (E)-3-(5-chlorothiophen-2-yl)acrylic acid gives the compound N-[4-(3-oxomorpholin-4-yl)phenyl]-(2R,4R)-1-[(E)-3-(5-chlorothiophen-2-yl)acryloyl]-4-hydroxypyrrolidine-2-carboxamide as colourless crystals, ESI 476, m.p. 151°.

Workup

  1. temperatureto cool
  2. customThe product which precipitates in the process
  3. filtrationis filtered off with suction
  4. customdried in a drying cabinet at 80° C.

Sources & evidence

ORD record
ord-4906c7c4f53a4330827aee94637050ce
Source dataset
uspto-grants-2011_03
Patent number
US07906516B2

Reaction notes

Loading…