Hydrochloric Acid → HCID 57627869, compound

HRID 1992273Notes

Reaction equation

HRID 1992273 reaction equation
Cl.[Br:2][C:3]1[CH:4]=[C:5]([C:9]([CH3:16])=[CH:10][CH2:11][S:12][C:13](=[NH:15])[NH2:14])[CH:6]=[CH:7][CH:8]=1.Cl.[OH-].[Na+]>>[Br:2][C:3]1[CH:4]=[C:5]([C:9]2([CH3:16])[CH2:10][CH2:11][S:12][C:13]([NH2:14])=[N:15]2)[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67025441HCID 67025441, compound

Product 1

HCID 57627869HCID 57627869, compoundYield 70%

Conditions

Temperature
100 °C

Procedure

A suspension of 2-[3-(3-bromo-phenyl)-but-2-enyl]-isothiourea hydrochloride (17 g, 52 mmoles) in 12 M HCl (53 mL, 640 mmoles, 12 equiv) is heated to 100° C. After 24 h, the solution is cooled to ambient temperature. The pH of the solution is adjusted to pH 10 with aqueous 2N NaOH and extracted with ethyl acetate. The organic layers are combined, dried over magnesium sulfate, filtered, and concentrated under reduced pressure to give the title compound (70% yield): MS (m/z): 285.0, 287.0 (M+1).

Workup

  1. temperaturethe solution is cooled to ambient temperature
  2. extractionextracted with ethyl acetate
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-194ada1bc7fc4721944e82f9b12d3915
Source dataset
uspto-grants-2010_01
Patent number
US07648983B2

Reaction notes

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