Hydrochloric Acid → HCID 72347155, compound

HRID 1363318Notes

Reaction equation

HRID 1363318 reaction equation
[OH-:1].[Na+].[Cl:3][C:4]1[CH:23]=[CH:22][C:7]([CH2:8][C:9]2[CH:10]=[C:11]([CH:14]=[C:15]3[S:19]C(=S)N[C:16]3=[O:21])[S:12][CH:13]=2)=[CH:6][CH:5]=1.Cl>>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:8][C:9]2[CH:10]=[C:11]([CH:14]=[C:15]([SH:19])[C:16]([OH:21])=[O:1])[S:12][CH:13]=2)=[CH:22][CH:23]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 72347159HCID 72347159, compound

Product 1

HCID 72347155HCID 72347155, compoundYield 95%

Conditions

Temperature
45 °C

Procedure

To a 20-mL scintillation vial fitted with a magnetic stir bar under a N2 atmosphere was added 3.5 mL of NaOH (2.0 M), and heated to 45° C. 5-((4-(4-chlorobenzyl)thiophen-2-yl)methylene)-2-thioxothiazolidin-4-one was added to the 2 M NaOH solution. After complete dissolution, the temperature of the reaction vial was increased to 60° C. over a 30 min period. The vial was subsequently cooled to 5° C. and cold 10% (v/v) aq. HCl solution was added until a precipitate formed (approx. pH 2-3). The resulting precipitate was collected by filtration, washed several times with water, and dried thoroughly under vacuum at 40° C. to give 3-(4-(4-chlorobenzyl)thiophen-2-yl)-2-mercaptoacrylic acid (379 mg, 95% yield). Note: 1H NMR showed a number of peaks in the aromatic region. The presence of the signal for the vinyl proton and the loss of the rhodanine moiety (i.e.; absence of the proton attached to the nitrogen in the rhodanine moiety) was used as an indicator of the desired compound. The material was used in the next step without further purification.

Workup

  1. customTo a 20-mL scintillation vial fitted with a magnetic stir bar under a N2 atmosphere
  2. dissolutionAfter complete dissolution
  3. customthe temperature of the reaction
  4. temperaturevial was increased to 60° C. over a 30 min period
  5. temperatureThe vial was subsequently cooled to 5° C.
  6. customformed (approx. pH 2-3)
  7. filtrationThe resulting precipitate was collected by filtration
  8. washwashed several times with water
  9. customdried thoroughly under vacuum at 40° C.

Sources & evidence

ORD record
ord-abd6b22a7f2240bc8c24516d4cb541c8
Source dataset
uspto-grants-2011_02
Patent number
US07884124B2

Reaction notes

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