Hydrochloric Acid → HCID 11759679, compound

HRID 1815493

Reaction equation

HRID 1815493 reaction equation
Cl[C:2]1[CH:12]=[CH:11][C:5]([CH:6]=[CH:7][C:8]([OH:10])=[O:9])=[CH:4][C:3]=1[N+:13]([O-:15])=[O:14].C([O-])([O-])=O.[K+].[K+].[CH:22]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[SH:31])([CH3:24])[CH3:23].Cl>CN(C=O)C.O>[CH:22]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[S:31][C:2]1[CH:12]=[CH:11][C:5](/[CH:6]=[CH:7]/[C:8]([OH:10])=[O:9])=[CH:4][C:3]=1[N+:13]([O-:15])=[O:14])([CH3:24])[CH3:23]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 96003Benzenethiol, 2-(1-methylethyl)-HCID 6149193-(4-Chloro-3-nitrophenyl)acrylic acid

Product 1

HCID 11759679HCID 11759679, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
70 °C

Procedure

To a stirred mixture of 4-chloro-3-nitrocinnamic acid (500 mg, 2.2 mmol) in 5 mL of anhydrous DMF with K2CO3 (911 mg, 6.6 mmol) was added 2-isopropylbenzenethiol (372 mL, 2.2 mmol) in 1 mL of DMF dropwise. The resulting mixture was then heated at 70° C. under nitrogen atmosphere overnight. Water (25 mL) was then added and the reaction mixture was acidified to pH=4 with 3N HCl. The cloudy mixture was extracted with EtOAc (2×20 mL). The combined organic layer was washed with brine, dried over Na2SO4, concentrated in vacuo to give the title compound as a viscous light-yellow oil, which was used for coupling with further purification.

Workup

  1. extractionThe cloudy mixture was extracted with EtOAc (2×20 mL)
  2. washThe combined organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-52af14d775b84026a7820109f15aaa7b
Source dataset
uspto-grants-2005_04
Patent number
US06878700B1

Linked notes

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